


Ain't Misbehavin'

by orphan_account



Category: Supernatural
Genre: Alternate Universe - 1920s, F/M, Forbidden Love, Gangster!Dean, Implied/Slight Bobby Singer and Ellen Harvelle, Jessica Moore and Jack Kline are Siblings, Kidnapped Castiel, M/M, Mainly Destiel, Minor Sam/Jess, New York, Period-Typical Homophobia, Period-Typical Racism, Period-Typical Sexism, Slow Burn, The Hunters are a Gang, The Novaks are a Family, gangster!sam, minor Dean/Lisa
Language: English
Status: Completed
Published: 2018-08-02
Updated: 2019-03-12
Packaged: 2019-06-20 19:51:04
Rating: Teen And Up Audiences
Warnings: Graphic Depictions Of Violence, Major Character Death
Chapters: 17
Words: 23,591
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15541740
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: "Ain't you just a cheery little angel?""I'm not an angel."It's 1926, and the infamous gang 'The Hunters' has practically taken over New York, dealing with things from speakeasies to...minor assassinations. Novak Industries, the wealthiest family and business in New York, is slowly but surely picking off gangsters. The Hunters need leverage-fast.. And Dean Winchester, gang leader of The Hunters, can't believe his luck when the youngest Novak walks right into him...This might just be a disaster.





	1. Prologue

**Author's Note:**

> Hello, this is my first entry on AO3! I posted this on Wattpad and thought I'd show it here, too. Updates weekly (hopefully), but I have life outside of fandoms (sadly). I'll do my best. Hope you enjoy! Feel free to share opinions at the end of the chapter. This is a short prologue, so I also might post the actual first chapter later today or tomorrow.

**Ain't Misbehavin'**

**_Oswin M. Cadwin_ **

_May 9, 1925_

Dean Winchester leaned against the filthy alleyway wall, light hair mussed under his dark fedora. His brother stood next to him, standing tall as he always did over everything. A book was in his hand, his own matching hat shadowing it in a gray darkness. 

"Whatcha' readin' there, Sammy?" Dean asked, leaning over towards his younger sibling. 

"It's called  _The Great Gatsby_ ," Sam informed him, looking interested. "It was only just published last month."

"What's it about?"

"Well--"

"Never mind. I don't care."

Sam rolled his eyes, laughing lightly as he slapped the book shut, hands folding across it. He placed it carefully in his jacket's inside pocket.

The sun shone down upon the brothers as they exited the alleyway, Dean looking around briefly yet cautiously to make sure the coast was clear for them. You never knew when you were a Hunter—anyone might recognize you.

New Yorkers surrounded them, everyone going about their daily lives, a few waving absentmindedly at each other before hurrying along again.

Dean motioned to everyone around them. "Look at this place," he chuckled, "everyone's all 'places to go, people to meet'. What the hell."  _They don't even suspect that there are a couple gangsters among 'em._

Sam crossed the street at an open spot, and the older Winchester followed in close pursuit. They knew right where they were headed—Harvelle's, the most out-of-the-way speakeasy in all of New York. Of course, the whole of The Hunters knew how to get there. It was practically the main base for their gang meet-ups. Ellen, owner of Harvelle's, was an old friend of the Winchester family. Her husband had been a member of the renowned gang, earning her a good name in the whole thing.

Dean then took the lead, stepping quickly in front of Sam and glancing this way and that as they walked inconspicuously among the others on the sidewalk before taking a sharp turn into another alley. There was a short staircase, and Sam was careful to avoid the broken stone step at the bottom. Dean almost tripped on it. Recovering, he slapped his hand onto the rusted handle of the door, before twisting the knob harshly to open it. The old door swung open--and the scent of alcohol and decent food hit them. Music wafted out of the door for a moment before the brothers slammed it shut, being sure to close it all the way. There were several tables and chairs, a busy bar on the nearest wall, and a makeshift stage on the other end where a couple people were playing music and a hired flapper girl was dancing.

"Boys!" They heard from the bar. Both turned to meet Ellen Harvelle herself half-smiling at them, her brown hair pulled back as she grabbed a couple bottles from the hidden counter beneath the top one. "Haven't gotten yourselves into any trouble, have you?"

Dean shook his head, smiling himself. "Nah, not lately. You seen Dad around?"

"Looking for John? In the back," she informed him, pointing to the stage. Sure enough, Sam and Dean saw their father's brown-haired head looking up at the stage as the flapper did a turn, fringe flying outwards. "I'm guessing you want these," she handed them each a couple beer bottles over the recently cleaned counter-top.

Dean took one with a nod of his head, and Sam thanked Ellen over the music that was steadily growing louder. The jazzy tune seemed to fill every single bit of the place, caressing their words when they tried to speak. Dean took the lead once again. Sam wasn't exactly on John Winchester's good side--he had wanted to abandon The Hunters, searching for a different, non-criminalizing life. That just didn't sit well with the gang's leader--their father.

"Dean!" John called over the songs, looking stern. "Where've you been? I gotta job for ya."

"Sorry, Dad," Dean sat down beside his father at the empty chairs near him, and Sam did the same, quite quietly. "We were checkin' out a... _sketchy_ ad in the newspaper."

"And what would that be?"

"Ah, just somethin' about takin' down the gangs in the area, gatherin' forces. Police stuff. We ain't got a lead at who published it."

"Well, figure it out. You know what this police propaganda could do to The Hunters. Remember who we're doin' this for."

"Right," Dean nodded. Mary, the boys' deceased mother. Killed in a fire set by the police when they were trying to drive out the Winchesters, who already had a supposed  _reputation_ for 'criminal activity'. John had taken the boys away from their small-town home in the southern area of New York and moved them to the capitol, big city of the state. John joined The Hunters, worked several jobs, and eventually took everything over when Dean was about fifteen and Sam was maybe eleven. The old leader had been stabbed in a classic street fight, and John was the natural choice. Dean was expected to take after him.

"Anyway," John sighed irritably, "I've run into some trouble. Seems to be that the cops are on m'tail."

_Ah, shit_ , Dean groaned inwardly. This seemed to happen every other week, and there was nothing he could do but follow his father everywhere.

"You all there?" John snapped, "I need you to pay attention, Dean! This gang ain't about to fall  _again_."

"That serious?" Dean muttered. His father was paranoid, but he usually brushed off these police incidents like a speck of dust.

"Yeah, that serious, boy. They're everywhere. Above us, around us, right beneath our feet. I swear it, the cops've multiplied since last time."

"Probably the damn propaganda," someone next to them commented. Dean leaned over his father to find Bobby Singer, one of his closest friends, a couple busy tables over. "It's everywhere. They  _'ave_ multiplied, ya idjit."

Both older men shook their heads, and Dean took a long draw of prohibited alcohol. Speakeasies were his lifeline. Sam was shooting nervous glances from John, to Bobby, and then to his older brother, who was winking at the flapper, who winked back. Sam knew her suddenly--Lisa, one of Dean's 'friends.'

"I should get goin'," John stood abruptly. The whole bar seemed to stop to watch him exit, the only sound Lisa's clapping shoes, which were now slowing down drastically as the renowned gang leader exited the building. Dean sighed to himself and glanced around before walking slowly after his father. A newspaper headline was tacked up on the left wall of the door:  _Lucifer Novak Abandons Novak Industries; Gabriel to Inherit._

A gunshot sounded.

Dean burst through the door at top-speed.

John Winchester, former leader of The Hunters, lay dead at his feet, blood blossoming like a twisted and wilting rose across his chest.


	2. Chapter One

**Notes for the Chapter:**

> This is the only double-update you get, since the previous chapter was a prologue. I noticed that I accidentally posted this story TWICE...that was an accident to do with glitches and wifi. Ah well, AO3 won't let me delete it now. Enjoy, and feel free to share opinions!

June 12, 1926

The day Dean Winchester first met his fate, his morning coffee was cold.

It wasn't a very good day.

He had woken up in his dingy apartment to a dusty-looking day, something like the sun had forgotten to clean out its house overnight. His rusted bedframe creaked as he became aware of his surrounding, the thin mattress pressing into his back. He pushed himself up, and his feet thudded onto the wood-paneled floor. His pajamas stuck to him with sweat. The mucky June day was bound to be a hot one.

"You awake? I got the coffee ready," He heard from outside his door. It was his younger brother, Sam. He chanced to hear him mutter something else.

"What's that, Sammy?" He called back, tugging off his button-up shirt and replacing it with a white long-sleeve. He adjusted the stiff collar.

"I said, 'It's bound to be cold at this point'," Sam replied casually.

"Damn, Sammy, how long've you been up?" Dean shook his head, swiftly pulling on black trousers before sauntering out the door and into the miniature kitchen.

The apartment wasn't much: The boys' small and gray shared bedroom, the kitchen where it seemed everything but the icebox and the broken-down stove was various shades of wood, the two-person table and chair set (also wood), and a couch shoved into the corner they called the 'parlor'. There was a crooked four-hooked coat stand, once again, a dark wood with chips in the polished surface. The best thing in the place was a half-decent radio they kept on the table, snatched up from the man in the apartment two doors down. The guy didn't need it, anyway--he was long gone.

"Couple hours," Sam replied, tilting the coffee pot to make the dark brown liquid rush out into a chipped blue mug. He handed it over to Dean, who took a sip and then wrinkled his nose in disgust and took a couple steps to cross the kitchen, setting the rejected coffee mug on the table.

"Nice work, Sammy," Dean said with a high note of sarcasm. "We should get goin'. Bobby said he has a job for us to follow up on."

"What? I thought Rufus took that one up," Sam protested, knowing halfway what was coming.

"Yeah, but he dropped it after the coppers nearly got 'im."

The youngest Winchester sighed. "I suppose, no use in him getting chilled off..."

The thought of Rufus Turner being killed was nearly sickening to both boys. They weren't exactly extremely close to the older Hunter, but Rufus was a friend of Bobby, and Bobby was practically the Winchesters' foster father. He had been there for them through thick and thin, getting John out of the caboose numerous times. After John had passed away...well, they didn't want their dear friend to lose another.

"Well, anyway, let's go," Dean grabbed his jacket off of the stand at the door and was out in seconds. Sam sighed, placed Dean's coffee mug next to the leaking sink, and followed after, his grey jacket already on. The job would be difficult—hiding at random locations until there was just the right opening...

 

~~~~~

Castiel Novak had awoken to his suit laid out and a greyish sunrise peeking in through the middle crack his drawn, dark brown bedroom curtains. A woman scurried in, glanced at him to be sure he was awake, tugged open said curtains, and scurried back out. She was, in Castiel's opinion, like a mouse: quiet and timid.

The youngest Novak glanced around his room briefly as he rose, slipped out of bed and into blue slippers, and peeled off his white pajamas. The dusty sun set a beam of gold across his otherwise dark room, setting off a bright shimmer from his full-length mirror that stood at the exact opposite end, propped up on a silvery stand. His dark oak dresser was next to that, and near that a matching wardrobe, and near that a wash basin and stool. The right wall to the window held his bed, which was as well dark oak, but stood out with the light blue sheets against the others brown-and-white room. The left wall was relatively empty, holding only a plain desk, lamp, and stiff wooden chair, as well as a carved gold cross on the wall above it.

This room pattern was mimicked by the rest of the rooms in the Novak mansion—Anna's, Hannah's, Balthazar's, Gabriel's, Michael's, Naomi's, Raphael's, Zachariah's, Hester's, Michael's, and Lucifer's. The only difference was that they all had differently colored sheets, Hester and Anna shared a room, and Lucifer's bedroom was literally barred from the inside. Lucifer had nearly been disowned the year before for 'betraying the family name' by refusing to inherit Novak Industries. In the end, he was only exiled, and now resided in Chicago.

"Castie-e-el!" He heard shouted from downstairs. "Castie-e-el! Where on earth are you?"

Castiel started to dress and wash up. The voice was his sister, Naomi, probably calling him for the family breakfast. He didn't particularly hate Naomi, but he didn't like her, either. She was rather stern, and quite the traditionalist. If it weren't such a shocking thing, Castiel was certain that she would have inherited the Industry. She could keep track of everything the factories produced—textiles, canned food items, and other necessities—with nothing but her clear mind and her crisply starched collar.

"I'm coming, sister," he called.

Sister. It was how he had always addressed her, as well as the other siblings he wasn't as close to. The only person he really called by name was his brother Gabriel, and he only directly addressed the others like such when the situation called for it. The blue-eyed man shook his head, buttoning his dark brown trousers. He studied himself for a moment in the standing mirror—brown trousers, white shirt, messy hair pressed down with water from the basin—and proceeded to rush out the door and down the hall as fast as his family dignity would allow him to.

"There you are, Castiel," his father half-smiled at his youngest son as he burst into the parlor, where everyone was sitting on the couches and cushy chairs with legs crossed and plates in hand.

"Good morning," he nodded his head at his family in turn, before taking a seat near Gabriel, who had an ungodly amount of strawberry jam on his roll, as well as a grainy white substance. He hissed a whisper, "Why are you putting sugar on bread?"

"Because I want to," Gabriel whispered back, a twinkle in his eyes.

Castiel rolled his eyes and accepted a plain roll from a maid, thanking her politely before biting off a small piece.

"Castiel," Hester said incredulously, finishing off a cup of warm coffee, "Where is your mass attire?"

He looked down, saw his everyday clothes, and excused himself to change. Mass, mass, mass. Every Sunday, like a 'good' family, of course. Within moments, he was bolting down the polished staircase again, directly towards the dark double doors. The rest of his family was already there, lined up according to age, with Naomi in the front, being twenty-four, and Castiel taking his place at the back, being barely nineteen. There was another setback: Hester had forgotten her hat, and had to rush away as well, grabbing it out of her and Anna's bedroom. She returned, with the brown accessory place on her head and the netting falling over her face and blonde hair.

"Let's get going," Naomi commanded her 'squadron', and the Novaks set out onto the suburban streets.

~~~~~

"I believe in one God, the father almighty, creator of Heaven and Earth..."

Castiel was reciting the words with vigor, and Gabriel was zoning out. Naomi elbowed Gabriel in the side, sharply, and the shorter person whipped his head up. "Of all things, visible and invisible..."

They recited the Nicene Creed, and the mass continued. Almost time for communion...Castiel counted communion as a way to tell that the mass was nearly over. Sure enough, communion came and went, and the mass was soon ending.

"Go forth for the mass has ended. Proclaim the love of God to your brothers and sisters."

The ending song began to draw out a tune from the organ, loud and abrupt, the congregation began to sing. Castiel mumbled the words, listening to a child who was crying a few pews ahead. 

He remembered a time when he was younger, maybe five or six, and had managed to slam his hand between the kneeler built into the pews. He had started crying silently, holding back any noise for fear of being noticed, but his fingers started to bleed a bit where he'd pinched them, and a very small, low sob escaped. Naomi, nine or ten, had grabbed him by the arm and practically drug him out, reprimanding him severely. He hadn't cried during mass again, nor had he hurt himself.

They left, each shaking hands in turn with the priest before exiting quietly. All the members of The Righteous One Church were upperclass and business-skilled people and their children, so the Novak family didn't stand out too much. Some businessmen that worked with Mr. Novak shook his hand with various forms of "Hey there, Chuck!"

While they walked down the path to the Novak mansion, Gabriel tapped his shoulder, pointing his vision to another family across the street. Castiel mainly noted a pretty young woman with light hair and a dress with just a bit of cleavage showing. Castiel wrinkled his brow at this immodest show of the body, seeing as they had come from the church. He also noted that her dress fell above the knees.

"Well, ain't she a Sheba?" Gabriel snickered into Castiel's ear. "That's the Kelly family. They're doing some hardcore business with Dad." Gabriel was well-informed on the matters of the Industry, as he would most likely inherit if someone else dropped out of the family.

"You shouldn't speak like that," the blue-eyed young man said through gritted teeth, "Father wouldn't approve."

"You mean...Naomi wouldn't approve."

"She is our sister, and is trying to do what's best for us."

What's best for us...

~~~~~

Castiel was on a walk.

Alone.

His tan trench coat flapped behind him as a light summer breeze gusted through the semi-busy street. He was sick of being with his family—it was driving him insane, really. He just wanted some fresh air (as fresh as it got in New York) and absense of his siblings' constantly peppering voices. He had managed to turn into a slightly... sketchier part of the city, but was happy with his findings, as it was less likely that he'd be recognised.

Or not.

All along the walls, random newspapers had been pasted, with bits of information about people and places and such. Stock Goes Up; Kidnapper Captured...Novak Industries Expands.

Castiel groaned inwardly. Yes, his father had bought another large portion of factory less than a month previously, nearly doubling the size of their canned foods region. Right on the cover of that paper was their whole family, serene smiles on their face, their father in the center. Castiel recognised himself on the inner left, Mr. Novak's arm around him. He was the youngest, the 'little angel'. He glanced around, peeled the paper off of the wall, and stepped a bit into an alleyway nearby, facing the street.

"Holy shit!"

Had he backed into someone? He started to turn. "I apologise, I just—"

A cloth came over his face.


	3. Chapter Two

**Notes for the Chapter:**

> Yeah, I posted another chapter and it hasn't even been a week. I'm too nice, haha. But-whoa! 132 hits! Thanks, guys!

Dean couldn't believe his luck.

Castiel Novak had literally just backed right into him. 

Sure, both Sam and Dean had seen him heading down the street, but they weren't sure if he was going to turn or what. Just in case, Dean had tapped a bit of chloroform onto a rag—just in preparation. Sam had given him a very disapproving look.

"What?" Dean rolled his eyes, "It's our job. You wanna save everyone's ass, you gotta do some dirty work."

Sam still looked extremely unamused.

Neither brother had even been sure if Castiel was going to come down the right street. However, he did—and quite literally ran into Dean.

"Holy  _shit!"_ Dean half-gasped. He heard a rough-ish voice apologise, but only for a moment, before his instincts kicked in and he silenced the other man.

~~~~

"What'a you boys got?" Bobby asked gruffly as Dean kicked open the door to The Hunters' secret hideout. 

They called it the Bunker, a large and hidden location that sprawled under a good chunk of the city. Dean was half-dragging an unconscious Novak in before Bobby actually noticed what was going on.

"What the hell?" Bobby was over in a flash. "You boys actually did it!"

"He did," Sam replied, his response clipped in annoyance.

"Either way," Dean grinned, "The Hunters ain't going down any time soon—not with one of Novak's best kids down."

"What is 'e, twenty or so?" Bobby queried.

"Nineteen, last I heard. Which room did'ya set up?"

The old gangster led them down several halls and then through a steel-locked door with a sliding window panel. Before opening it with a slight rusty shove, Bobby checked the window.

"Wanted'a make sure there ain't another guy in there. You know how people get when you boys do somethin' right," Bobby rolled his eyes just slightly, and led everyone in there, Dean dragging Castiel.

Dean dragged Castiel to the wooden chair in the center, pushing him into it and then accepting some ropes from Bobby. Sam stood on the sidelines, distant as Dean tied the innocent man to the seat, hands, knees, elbows and ankles all bound. He hesitated before deciding against tying his head to the back, as well. There wouldn't be a heavy risk of this kid chewing the ropes off.

The light strung up over the chair was beating down on both of them as Dean finished, stepping back. Sam gave Bobby a curt nod before leaving abruptly, Dean throwing him a look.

"Nice work," Bobby said quietly to Dean, before going after the younger Winchester.

Dean sighed and pulled a dusty stool from the very corner of the room, sitting on it a few feet in front of the Novak, facing him. The small light above Castiel's head set off a glow around him that Dean couldn't quite place. He shook his head, thinking about what his plan was now--obviously, a few Hunters would send out the ransom letter; probably deliver it themselves. He himself would be the one to question the captured man. 

Suddenly, the pair of eyes across from him snapped open. Dean focused his attention on the Novak, whose face was the picture of confusion for only a moment before switching to minor panic.

"What the hell do you want with me?" He asked sharply.

Dean leaned closer, looking him dead in the eyes. He hadn't noticed the shade of the younger's eyes beforehand—sharp and blue, like a clear, late day sky. Well, not a New York sky, which was full of gray smoke being pumped into the sky by the various factories. The factories owned by Novak Industries, of course.

A flash of anger came over Dean Winchester at that thought. "I don't think I'll be answering your question," he replied shortly, "but you'll be answering mine."

Castiel clamped his mouth shut, indignant.

"C'mon," Dean glared, "work with me. You don't want you dead...I don't want you dead..."

"Then why am I here?"

"I told you, I ain't answering your questions."

"Then start asking," Castiel growled.

Dean's fury flared again. His hand traced the pearl-handled pistol on his waist as he got up, standing over the dark-haired man. He had to keep calm--it would do no good to have a ransom to someone whose son is already dead.

"Alright," the older Winchester began, "enough talk. What's your inheritance?"

He was silent again.

Dean swiped a fist across his face, hard and fast. Castiel's head snapped to the side. He coughed quietly and adjusted his neck. Dean could see the discoloration of a large bruise appearing on his right cheek.

"I said," Dean pressed his hands into the arms of Castiel's chair, " _what is your inheritance?"_

Castiel gritted his teeth. "Why do you care?" He snapped in his deep voice.

"Because I wanna know how much your rich daddy really cares about you," Dean taunted, inches away from Castiel before pushing back and standing over him again. 

The single dim light hung low and was nearly burning Castiel's head. The dark-haired man hated his predicament—apparently, as he could piece together so far, he had been kidnapped because of money. Cheap.

"You better start thinkin' about answering my questions, Novak," Dean backed towards the door, "because I'll be back soon."

The eldest Winchester swung open the heavy door, and Castiel watched it slam shut behind the dark-suited man. He groaned inwardly, hints of panic threatening to bubble up into a yell. How could this happen? Sure, he'd always been wary—that was just how it was, being the child of a big-time businessman. Yet...this felt strange. Like this man who'd kidnapped him had a deeper meaning besides ransom. Castiel had felt it, looking at those bright green eyes. It was almost like the Novak family had personally attacked this wayward gangster.

But Castiel could feel no pity for him. Not for the man who captured him, tied him up, and hurt him.

The door opened again, and the Novak looked up to see yet another apparent gangster in the doorway, carrying a small glass of water in one hand. Castiel noticed his hair, first of all—brown and in need of a haircut in any respectable opinion—and then his brown eyes, pup-like and nearly caring. 

"I'm Sam," The new man started. "I, uh...brought you some water." 

He started untying Castiel's right arm, and then gave him the water. The kidnapped man was suspicious, but soon discovered that he was overwhelmed by thirst. He didn't thank Sam, but tipped his head back and downed the cup. He didn't  _feel_ poisoned. He decided that Sam was much kinder than the previous occupant of the room. He even noticed Sam grab the stool and climb up on it behind Castiel, adjusting the low-hanging, burning light. The heat disappeared.

Suddenly, footsteps came—heavy and unforgiving. Sam darted off the chair and snatched the glass from Castiel's hand, messily tying it up again. He burst out of the room, moving quickly. The ransomed Novak heard intelligible yelling from the echoing halls outside before the almost soundproof door slammed shut.

Castiel was alone once again, tied up, ransomed, and secretly very afraid.

**Notes for the Chapter:**

> This has been a game of how-many-name-descriptions-for-Castiel.


	4. Chapter Three

**Notes for the Chapter:**

> The 1920s age of majority is 20-21, just a note.

What seemed like days later, but was only hours, the door opened again.

Dean stepped inside. Castiel had his head hung low, seemingly half-asleep. This seemed to please the Winchester as he fingered a gun on his hip. He crept over in front of Castiel, and then quite suddenly whipped out his gun in one swift motion, holding in about five inches away from the ransomed's drooped head. At the click of the lever, his eyes snapped open, and he stared down the barrel of the gun, seemingly fighting the urge to yell out.

"Well, look at that," Dean drawled, "fancy seeing the angel awake."

"It really pisses me off when you say that."

"Well, I'm not bothered by what pisses you off."

"I'm still not answering your questions."

Dean aimed the weapon more accurately at the center of Castiel's forehead. "Look, kid, I got a gun aimed at your head. You're gonna answer my questions, or get a slug to the brain. Savvy?"

"I'm not a 'kid'. You're barely older than me," Castiel studied him lightly, before looking down once more.

Dean slapped the barrel of the gun on the corner of the Novak's face. He winced, quietly, but it was enough to give Dean the pleasure of getting a reaction.

"Now," he instructed, as though speaking to a child, "let's all play nice. What's your inheritance?"

Castiel seriously considered not speaking again. However, it was only day two of being captured, and already there was the threat of a bullet in his head. He swallowed, daring to move his eyes up to Dean's face.

"A quarter of the business and $90,000."

"Anything more?"

Castiel paused. He'd certainly discussed this all with his father more than once, but in this desperate time, all conversations fled his mind.

"I said,  _anything more_?"

"That's all."

"You bluffin'?"

"That's all, I swear!"

The gun was dangerously close to his head. Dean continued on.

"You got any knowledge of your father's underground business?"

" _What_?" Underground business? The youngest Novak had never heard of any such thing. As far as he knew, Chuck Novak simply sat at home signing papers and contracts, as well as occasionally wandering throughout his various circuits of textile and canning factories.  _What can this gangster possibly mean?_

"Answer me straight, kid!" Dean pushed the gun forward again.

"I don't know anything about that," he answered, completely honest yet again.

Dean seemed to pause, wavering the gun slightly. "Alright, so you don't. Well, your daddy thought it would be a swell idea to go around the state, uprooting the highest companies."

"You mean...gangs."  Castiel made sure to not say this as a question—he'd rather not get whacked with the butt of a gun again.

"I think I prefer  _higher companies._ "

"I don't care what you prefer."

Dean nudged him harshly with the gun again. Castiel could feel his face swelling up.

This would be another long day.

~~~~

"I don't care where you  _think_  he is! I want to  _know_  where he is!"

Naomi sounded horridly angry, screaming at the press as they gathered on the doorstep of the hailed Novak mansion. The other Novak children had varying  expressions on their faces—Anna looked absolutely distraught, while Balthazar's face was void of feeling, and Gabriel was unreadable.

Chuck had officially reported Castiel as 'Missing' that very evening, though it had now been only two days. This had caused a wildfire to spread across the news—this information immediately attacked radio reports, and was being typed into newspapers faster than the typewriters and printers could even keep up. By dawn,, Mr. Novak knew that every newsie in New York would be yelling on the curb sides: 'Novak family tragedy, read all about it! Extra!'

A man with a bowler ran up, camera in hand. "Mister Novak! Whatcha got to say for the people? You got any reports on your son's whereabouts? It's been rumoured that he's run away—!"

"I can assure the  _Times_ that he did not run away. We are almost certain that foul play was involved in my son's disappearance." 

Chuck acted rather composed, but he wanted to scream just as much as his daughter when the camera went off, snapping a picture of the family gathered in the doorway. Gabriel herded Anna and Hester back inside, both girls now crying heavily at the thought of their brother being lost.

~~~~

"Dean!"

Dean looked up at his brother, now sitting at his desk and organising their first ransom letter.

"Whaddaya want, Sammy?"

"It's made the papers."

"And the radio can't be on without that boy's name bein' mentioned," Bobby added, wandering in. "You sure you boys can handle this? Dean, you're not even an adult yet. And Sam—" Bobby looked almost pained. Sam was only sixteen.

"We can handle this, Bobby; we ain't behind the eight ball yet," Dean assured the older Hunter, "I've been ready to take charge of the gang since I was eleven. We'll be fine."

"I just don't want you ending up in the big house..."

"We'll be fine," Dean said again, nodding.

"Alright, but come to me if you need any help. Promise that."

"Okay, okay, I promise. I'm finished with the letter. Sam?"

Sam took the envelope, donned his hat, and started out of the Bunker, feeling determined—but somewhat regretful at what he was doing.

~~~~

_Novak-_

_I'm sure you're wondering where your boy is by now. He is unharmed, but won't be for long if you don't listen. Now, read this carefully:_

_Stop your gang intervening. I'm sure you're learning that if you don't bother us, we don't bother you. We demand a fee of $90,000._

_These small guidelines must be met for your son's safe release. The $90,000 will be sent via envelope and hand-delivered to a man who will be on 2nd Street NW. Do not send yourself. Do not send one of your rookies. Send one of your children. They will not be harmed. A month after this payment,if there are no signs of your gang intervention, Castiel will be safely returned to your mansion._

_Think carefully. Castiel Novak's life is in your hands._

 


	5. Chapter Four

**Notes for the Chapter:**

> I'm a day late on updates! Whoops.

"Stars above..." Hester whispered, a hand flying over her mouth in shock.

"This is outrageous!" Mr. Novak yelled, slamming the little slip of cheap paper back down to the expensive mahogany desk. "The very idea!"

"Father, what will we do?" Anna asked sincerely, huddled close to Hester.

"I'll blast those goons into hell, that's what I'll do!" Gabriel shouted quite suddenly, his hand smacking the table soon after the paper. "Maybe they got the bulge, here, but I'll fill 'em with daylight, either way!"

"Gabe," Mr. Novak reprimanded in a harsh voice, "Quiet down. And I don't want to hear that street slang in my house."

"Sorry to say this, pops, but close your head. We've got a few bigger issues than perfect grammar, at the moment."

"Gabriel!"

"I said, shut it! I'm getting that 90,000 out of my own account!" Gabriel turned on his heel with a sharp  _squeeeak_ , leaving a small, black mark on the floor before exiting the office room promptly.

~~~~

_3 Days Later_

"You clear?" Sam whispered quickly as Dean slipped through the thick door to the bunker. 

"Yeah, it's all good, Sammy."

"Damn it, why did you take so long to check the payment?"

"Remember that one guy we had in business once; name was Benny? Ran into him. He got tripped up by a copper last month, apparently."

"Ah...right."

"Oh, by the way--they still haven't paid us the cash. So keep an eye on Castiel."

 Sam wasn't quite sure what he thought of Benny, but  _Dean_ knew what Sam thought of Benny--he was a friend of Dean's, and he hadn't murdered anybody they cared about, so he was probably okay. 

"Hey, you should probably go talk to...him." Sam nudged his head towards the back area, indicating their 'prisoner'. "He's...going into some sort of shock. Bad shock." 

"Damn straight, he is," Bobby called down the echoing hall, coming from the direction of Castiel. "The boy's real knocked today, I can tell ya that. Dean, you're up."

Dean sighed quietly as he walked past Bobby, hands in his black jacket pockets, fiddling with a crumpled piece of paper. It was like some sort of kiddie relay race--Sam went, tagged Bobby, Bobby went, tagged Dean. And Dean? Well, he was wondering how bad this 'shock' would be. They'd done ransom before--a girl who went by the name 'Meg'. That was before John Winchester died, and they'd managed to catch someone from an opposing gang, Hell's Demons, who was snooping around the Bunker. Dean shuddered a bit internally as he remembered that time. His own brother had nearly been seduced by that Demon.  _Ugh_.

As the eldest Winchester opened the door of the vault-like holding area, he heard quiet sounds of hyperventilation, echoing softly in the room.

"Castiel?" Dean said in a calm but commanding voice, stepping closer to the younger man, his shoes clicking on the hard surface of the floor. "How're you doin'?"

Silence. Castiel shivered in the chair, rocking his head a bit.

"Listen...Cas. Can I call you 'Cas'?"

No reply.

"Alright, Cas. We sent the letter. We ain't gonna hurt you. You know that, right?"

More quietness, taking up the room more than Dean's faded words.

"Seriously, Cas. Work with me. I didn't--I didn't wanna take you. I never  _wanna_ take anyone, but we have to do what we have to do. You understand family, right? You have one hell of a family."

Castiel looked up at Dean, his beryl blue eyes vacant and staring. Dean decided to take on a different tactic. If the ransomed boy stayed like this--who knew how long his sanity would stick around, and then they'd have to deal with backlash from the Novaks when he was possibly, eventually, returned.

Dean got down on one knee, leaning a bit to face the Novak closely. "How many siblings do you have, Cas?"

A bit more quietness. Then--

"Eleven."

Dean whistled. "Damn. Eleven? I just got Sammy. You might've seen him. Tall cat, looks like a flapper girl?"

Castiel nodded.

"Awesome. You ever had a girlfriend?"

"Why are you...asking me these questions?" Castiel replied right back, his deep voice rolling through the small room.

"What, I can't just get to know you?"

"Well, you did kidnap me, put me up for ransom, and lock me in a cell in the middle of--God-knows-where."

"Uh..." Dean smirked. "Small details, Cas. Now, you ever had a girlfriend?"

Castiel sighed in a gust of air, but obliged to the query. "No. Not a real one, anyway."

"Do tell."

"I don't feel that this information is necessary to divulge."

Dean nodded. Yeah, he'd been yelling like a madman at this same person just a few days ago, and now he was acting like an old pal. He could understand this, and decided not to press any further for replies. Really--he  _kind of_ felt bad about how he'd treated Castiel, but business was business, and he had to carry on with it in his dead father's name.

"Alright. I had a girlfriend. Still do...maybe? I ain't got a clue, really.  _Quite_ the babe. Name's Lisa."

Castiel just nodded again, leaning back in his chair a bit more. Dean noticed the rawness on his wrists as the ropes adjust slightly. Maybe he'd do something about that...tomorrow.

"Dean!" the Winchester heard his name being called. "Any luck?"

"Yeah!" Dean called back. Castiel gave him a suspicious glare, and Dean rolled his eyes. "Relax, Cas. We were tryin' to make sure you didn't go crazy."

"Hm."

"Well--I'll talk to you later." Dean put his professional, slightly shady face back on, turning away and disappearing out the door with a  _chink_ of the thick metal.

~~~~

Dean laid on his bed that night, half-asleep, half-concentrating on the situation at hand. If the money wasn't sent, what would they do with Castiel? Keep him there forever? Of course, incidents like this had to be dealt with carefully and patiently. The money could be on its way. Either way, he couldn't back them out of the deal, now. That would make the gang look weak, and the Hunters were known for being strong. He'd give it at least another two weeks before actually get truly concerned.

 _Stop feeling like an amateur_ , Dean reprimanded himself as he mulled over these worries.  _Don't get all uptight over a minuscule problem like this._

Eventually, he forced himself to sleep.

**Notes for the Chapter:**

> Hope you enjoyed! Feel free to leave your opinion, I always love comments!! Thanks for all the support so far :)


	6. Chapter Five

**Notes for the Chapter:**

> I'm reaching the end of my pre-written chapters...time to get working again! Thanks for the support~

_June 25, 1926_

Dean slammed a hand down on the rickety desk he had in his room. 

"Damn it!" He yelled, huffing angrily.

Sam made a disapproving Sam-face from across the room. "They didn't decline to pay upfront, Dean. They just haven't paid us  _yet_. Why is this bothering you so much?"

"Because I want those damn brunos off my back, already! It's been over a week--I wanna open the door to the Bunker and not have to worry about seein' some guy with a buzzer ironed on his shirt!"

"...You always have to worry about that, Dean. We're in a  _gang_  in  _New York_."

"Yeah, but now that we have that Novak kid here...it's like everyone's on some high alert. I can't go down to Harvelle's without gettin' ready to point a gun around the corner."

"Alright, so there are a lot more coppers around here than usual," Sam sighed, "But we just have to deal with it. Hey, have you thought about letting Castiel into an actual room?"

Dean was quiet for a moment. No, they didn't keep him locked up all the time--it wouldn't do anyone any good if the Novak's legs didn't work when-- _if--_ he eventually was released home. He was let out, allowed to walk around the room for a bit, eat, so on. Twice a day, and that was it. Bobby had been talking about making it three times a day, but Dean dismissed that idea--the 'kid' slept on the ground at night instead of in the chair like before, so didn't that count as a break?

"Look, Dean, he's been staying in a fairly cold, very dark room for over two weeks now. Aren't you feeling any empathy at  _all_?"

The eldest Winchester shrugged absentmindedly, pushing in his chair as he rose and walked out the bedroom door. Sam followed in close pursuit, continuing his argument.

"He's completely distraught, Dean," Sam pushed, "don't you understand that? How would you feel if  _you_ were kidnapped on the street? Half-beaten and torn away from your family?"

Dean whipped around to face his younger brother, his face the picture of anger. "I've already been torn away from my family!" Dean yelled, his furious voice echoing through the long hall. "Mom's dead, Dad's dead, and it's all because of that damned Industry! I get it, you didn't know Mom, you didn't care about your own father, but damn it, Sammy, I do! And I don't want the whole gang goin' down because we go easy on some clammed kid who manages to escape!"

Sam now had an equal flame of temper in his brown eyes, staring at his older brother face-to-face. It miffed Dean in a minor way that his sixteen-year-old brother was taller than him.

"I just don't want you making a stupid mistake this time around," Sam said in a low, testing voice, before turning on his heel and going back down the hall, probably to sit in his own room and think of ways to convince Dean of his stupidity.

~~~~

That night, Dean dragged in an old mattress and laid it on Castiel's floor. Before the blue-eyed boy could say a word of his current confusion, the gangster left--leaving the nineteen-year-old to ponder this sudden event, before giving in to his exhaustion of waiting for so long and collapsing on the lumpy material, falling asleep much quicker than usual.

Dreams of gun barrels and a mattress stuffed with knives clouded his rest that night.

~~~~

Dean woke up sometime around one P.M. to Ellen Harvelle whacking him over the head. Gently, but enough for him to fall out of his chair at one of the mismatched tables in the underground-famous speakeasy.

"We're openin' soon," Ellen told him sternly, glancing over her shoulder as she rummaged in a cabinet, "So get up, at least."

Dean groaned, pressing the heels of his hands to his green eyes. He had a serious hangover. What had happened? He remembered stomping out of the Bunker, stumbling into Harvelle's, and ordering...what was it, again? Three drinks? Four? But he downed them all (while ignoring all attempts of conversation from Jo) and passed out at the table.

He tried standing up, feeling like the floor was made of gelatin. He was Dean Winchester, though, and always got over his hangovers like a man, so he straightened his back and flashed Ellen a smile.

"Watch out for the broken glass," Jo called from across the room, stepping out of the back supply closet with a broom in hand.

Dean looked down, see a shattered alcohol bottle splayed across the floor.

"Yeah, you nearly crashed your head into that, kid," Ellen sighed as she watched her daughter move to sweep up the mess. "Then you swiped it off the table."

"Like a boozehound," Jo muttered as she finished her work and headed to the bin. Ellen shot her a look, shaking her head.

"Sorry about the mess, Ellen," Dean sighed apologetically. "It's been a rough couple 'a weeks."

"Bobby told me about your latest...job. Anything I can help with?"

"Nah, I got it covered. Hopefully the ransom is paid soon, or we're all gonna be found out and sent to the big house."

"Well...for your sake, Dean, I hope that doesn't happen...for Sam's sake, too." Ellen placed a hand on Dean's shoulder for a moment, before turning back to her bar and placing things in order for opening time, when all the back-alley baddies would start trickling in to drown their worries in strong whiskey.

 _For Sam's sake?_ Dean scoffed silently. Sam, from what he could tell, didn't even want to be a Hunter. Therefore, he wouldn't want to be associated with Dean, the Hunters'  _boss_. Well, 'boss' used loosely. Bobby kinda steered the matter. And for that, Dean was grateful.

He could never do this on his own. Family mattered, even if you were a hell-bent, hell-bound New Yorkie gangster.

~~~~

Somehow, Dean ended up meandering back to the Bunker, where Sam greeted him with a silent nod of barely-there acknowledgment and Bobby dragged both boys off to discuss an advancement on a different case--a druggie they served regularly had been shot in the head three times by someone that  _wasn't_ a copper. Dean, head already crowded with other thoughts, shoved this in his mind to consider later on. He thanked Bobby for the update and headed out of the main office, turning the corner and starting for a specific room he knew pretty well.

He opened the metal door, giving Castiel a half-sarcastic smile.

"So, whadda you wanna talk about today?"

**Notes for the Chapter:**

> See y'all soon :-)


	7. Chapter Six (Previously Unpublished)

**Notes for the Chapter:**

> So, I made a mistake, and this chapter was skipped in the publication of my chapters from Wattpad. Here it is now!

_June 29th, 1926_

It was another three days before they heard from the Novak family. One of the gang members, Gordon, had passed off two pieces of paper to Bobby--one a long sheet, and another a scrap that seemed to have been torn off of the end of the former, leaving both with a rough edge.

"They were delivered by Gabriel Novak," Bobby announced as he pressed both notes out on the kitchen table, where Dean was popping open a beer he snagged from Harvelle's and Sam was drinking a cup of coffee. "So at least they kept up on that end of the deal--havin' a Novak kid deliver it. But...this ain't good news, boys."

"What'd they do?" Sam sighed as all three crowded around to read.

_'Gang'-_

_If you think I'm going to send you 90,000 dollars in return for my son who you had_ NO _right to kidnap from me, much less follow by keeping him for another month, you're wrong. I'll give you 10,000 and you'll return him immediately. I have men all over this city--all over this state!--who are scouring the area for Castiel, not to mention that the police and the press have both been alerted to the situation. I have the mind to enlist a private investigator soon, too. As for my industry stomping out the gangs?_

_Good riddance._

_-Novak_

Dean actually laughed at that.

"This guy's hilarious! He thinks he can just drop 80,000 and it'll be sunshine and roses for everyone?"

"Not to mention that he _told_ us he's enlistin' a dick," Bobby shook his head.

"Well, at least now we know to be on the lookout," Sam commented, folding up the letter and placing it securely in his jacket pocket.

"Wait, there's another one. Different writin'."

_To who it concerns_

_I'm writing this literally as fast as I can and I thought you oughta know that I'm sending the money so it'll be to you as soon as I_

It faded off the shred of the page for a moment, and the writing continued in a cramped corner.

_can get my account open so keep_

_Cassie safe_

_shit outta room_

_-Gabe_

"'Cassie'?" Dean half-laughed. "I'm usin' that."

Sam gave him a disapproving look. "So...Castiel's brother is planning to pay the ransom..." he sighed. "Are we accepting it, then?"

"I mean, I don't see why that ain't allowed," Bobby raised an eyebrow beneath his worn baseball cap he wore on days 'off'. "It's still cash we're gettin', and we're kind of in debt to some branches in Chicago..."

" _Shit_ , I thought we took care of that," Sam hissed, thinking of the gangs in Chicago that they'd dealt with in the past.

"Nah. Hm, based off this guy's writin', I'm not sure if he'd be able to even _find_ us again, much less get his own bank account open..."

"Yeah, not too eloquent for a fancy Novak, that's for sure," Dean scoffed. "Whatever. Dough's dough. Let's just see if he actually pays up."

"Hey, you planning to tell Castiel the news?" Sam questioned, looking over to Dean, who was leaning over the notes again.

"Eh?" Dean looked up from his loose concentration. "Why would I do that?"

"Uh, because he deserves to know that he'll be getting out," Sam was the one to raise an eyebrow this time, "And that his _brother_ contacted us. Besides, no one's checked on him today."

"That boy was in a bad state yesterday..." Bobby trailed off, shaking his head. "You'd think he's goin' mad in there. You go, Dean. I gotta check up on our other deals. Think we can scrounge up some cash around here somewhere..." he walked away, heading down a well-lit corridor. Sam gave Dean a grimace, then followed Bobby at a quickened pace.

Dean headed to Castiel's metal door, muttering something to himself about ' _I'm_ the one going mad here', and _'Deserves_ to know, it's a _privilege_ to know in his position...'.

He twisted the knob, pushing the door open. A pair of blue eyes, much dimmer than before, looked up--and Castiel flinched upon seeing Dean in the bright doorway.

"What do you want?" He whispered, looking down. His hands were tied at the wrists  and placed in his lap. He was slouched gently in the stiff chair.

"I wanna talk to ya," Dean smirked, "That reason enough to enter a room in my own house?"

Castiel mumbled something, but turned his head.

"What was that?"

The hostage looked up, an alarmed expression on his face. "Nothing." He seemed to be attempting to sink into his chair.

Dean raised an eyebrow (it was a common theme that day), moving forward. "Alright, alright. So...Sammy wanted me to tell ya somethin',"

"And that is?" Castiel queried quietly.

"Your Pops sent us a letter. Basically, he didn't agree to the terms."

Castiel's face fell.

"But your brother sent a note, too. Gabriel. Somethin' messy about paying for your ransom when he can get his account open."

His face brightened a bit, but then darkened again. "Ah...if, yes."

"What, you know somethin' about that? The account?" A bit of an edge crept into Dean's deep voice.

The hostage answered immediately, looking thoroughly afraid of any backlash. "The accounts are controlled by my father. They're all mainly under his name, but he titles them differently. If he doesn't want Gabriel to have access to an account, he tells the bank. That's all I know." He spoke in a rushed voice, as if afraid he would be hurt for not speaking within a time limit.

"Calm down, Cassie. I ain't gonna hurt ya."

"Well, your previous actions prove otherwise...and...don't call me that."

"What, 'Cassie'?"

"Don't."

"Fine, fine." Dean rolled his eyes. He grabbed the stool from the far corner, sitting down. "How about we have a talk again?"

Castiel grimaced. "I assume I don't have a choice."

"Nope. So, what do ya think of Gabriel, anyway?"

"He's a kind brother. Probably nicer to me than the others, but...I love them all the same."

"Come on, you gotta have some bias with all those siblings you have."

"God has no preference among his people, and neither do I."

"Well, he liked Jesus best, didn't 'e? I mean, I don't know much about your little fanatic religion, but--"

"Jesus is a part of God."

"Yeah, yeah. Okay. So, what are your siblings' names again?"

"Gabriel, Naomi, Balthazar..."

Dean listened as Castiel listened off his various family members, looking just a bit less terrified. And really, Dean preferred him that way.


	8. Chapter Seven

**Notes for the Chapter:**

> Sorry for taking so long! Here you go!

"Mr. Novak must've been crazy when he named his kids," Dean commented randomly, looking up slightly from the Sunday paper that he hadn't read when it came out four days previously. Bobby had nicked the paper off of the kid at the corner who hadn't sold that many, and had managed to get it for half the price. Times were tough, barters had to be made, and children were no exception.

"Uh..." Sam looked up. "Sure."

"No, seriously. 'Castiel'? That's not even in a Biblical text. All the others have a religious match. The guy was a dope fiend when Cas was born."

Sam wasn't going to mention the excessive use of 'Cas' lately. "I suppose. Oh, so get this--the Men of Letters are still refusing payment for what we did in April."

"Seriously?" Dean scoffed. "They ain't even a gang, at this point. They had to call in a whole other branch just to knock off some fella who was wavin' a pistol at them."

"I heard they did the same thing with the Chicago Demons."

Dean looked surprised. "What, with the Demons, too? I suppose that makes more sense, since all they are is a bunch'a droppers and dope peddlers, but - refusing pay to _them_?"

Bobby strolled in, a shining cloth wrapped tightly around the pistol he carried in both hands. "Well, they ain't in any sort of financial need, anyway. Us, on the other hand - we need to get that cash in from them _soon_ , or the gang's shot. We did that job fair and square. The guy's dead, ain't 'e?"

"Pretty dead, last time I saw 'im. Anyway, what's up with the Men of Letters and passing off all the dirty work to others? They're all packing heat, but they never use their weapons unless they're bein' directly attacked. I ain't gonna be their personal trigger man unless they start payin' up."

"I doubt we'll get payment before Chicago does, anyway. All's we can do at this point is wait. The Demons'll take care of it at some point..."

"I hope they learned their lesson from the _last_ time they waited ten months to pay them," Sam said tersely, lips drawn in a thin line as he looked down at his book once more. 

Yes, truth be told, it was suicide to wait ten months to pay the Chicago Demons. They had an elite group of gangsters they called their 'Hell Hounds' - Men and women they hired who scouted out the deal-maker and tortured or killed them to get the money. Dean had witnessed it happening far too many times. The women were femme fatales at their finest, and the men were downright sneaky. You turn away, and suddenly - you're dead.

Dean tried to move to, well, _happier_ thoughts. He might go down to Harvelle's later that day and watch Lisa. She had a show booked that night. Not that it was particularly difficult to find her shows - she was booked three times a week at Harvelle's, and had two other shows at another, much more sleazy-looking speakeasy. Dean never really went there, though, so he stuck to the three day schedule the flapper held in familiar territory.

"Anyone checked on Castiel today?" Bobby asked absentmindedly.

"This morning, yeah," Dean nodded, rising from his chair. The library was starting to feel dreary and boring.

"How is 'e, then?"

Dean considered for a moment. Really, he couldn't tell. "Ah, same as always. You know. Hey, I'm off to see Ellen. I'll talk to ya later. Be back soon."

"Alright, see ya then." Bobby barely got the words out before Dean was clambering up the stairs to the door.

 The older man gave Sam a look of confusion. Sam just shrugged.

~~~~

Ellen barely had to look up as she heard the door open.

"Well, good afternoon to you to," the bar owner raised an eyebrow, "You're actually here while we're open."

"Yeah, we were occupied with some research." He sat at the nearest table. A few lazy patrons were chattering slowly in the corner, where Jo was handing someone a beer. They said something, and she promptly took the beer and broke it on the table, causing a loud uproar.

"Damn it, Jo..." Ellen half-laughed. "I told you, she's gettin' into that flapper trend."

"I can see that," Dean smirked, eyeing Jo's skirt that fell above the knee. Ellen gave him a wary look. "Ah, come on," Dean laughed, "She's too young for me."

Ellen shook her head, but had a small smile on her face. "Your usual, then? Enough booze to get you killed?"

"Ya know me too well."

Soon, Dean had popped the cap off a beer, and was seated comfortably with his feet up on the table (Ellen had no cares for how he treated the place, as long as nothing broke) and a bottle in his hand. He didn't know how many people had drifted by him, greeting him sometimes, or giving him glares another.

He had soon finished off his second beer. He checked the dingy, smoke-smeared clock, and was a bit surprised to see that it was already five o'clock. He had been there for two hours?

Suddenly, the small 'stage' in the back of the room lit up,  and the familiar clicking of a pair of shoes was heard. Lisa Braeden appeared, hair curled up tightly and dress even shorter than Jo's. Speaking of Jo, Dean saw her silhouette in the back, adjusting a record. They rarely had anyone there to play music, and if they did, it wasn't great. Records, Ellen had found, were just easier. A fast, jazzy beat came up, and Lisa started her performance, the fringe on her dress flying with the beat.

Dean leaned back in his chair again. "And I guess I'll be staying a bit longer."

~~~~

Two more bottles and five performances later, Lisa was off the stage, wandering around for her break. 

"Hello, Dean," she smiled at him, coming over to his spot.

"Hey, Lisa," Dean winked.

"Happy to see you made it here. I haven't seen you around as often."

"Well, you know me. Always busy."

"You got a job, then?"

"Sure did. But that's all confidential, of course."

"Oh, I know." Her voice lowered a bit. "Dean, why don't we go out back?"

"Well, it's like you read my mind."

Ellen watched Dean follow the dancer, a sigh building in her throat and escaping. "That boy...drowning his thoughts in booze and Lisa. Wonder what's got to 'im now."

~~~~

Dean arrived back at the bunker well into the night, and was surprised to find Bobby still up.

"Hey, Dean," he said gruffly, looking up from the paper he was studying again. "And what'd you do this time?"

"I told ya," Dean sat opposite of him, eyes looking clouded with alcohol. "Been 'a Ellen's."

"What happened to 'be back soon', then?"

"Why does it matter? I do want I want. I'm an adult."

"Yeah, and for the first time in a while, you're completely drunk. What's gettin' at ya, boy?"

"Nothin', nothin'. C'mon, we got some research to do, right?" His words were slurred.

"Sam and I finished that two hours ago, when you were _still_ out. Is this about the job?"

"Whaddaya mean?"

"The job. Kidnappin' one of the Novak boys?"

"Why'd I be bothered by tha'--that?" Dean attempted to speak more clearly.

"Well, I know the last time we had a job like this...well, it really messed you up good."

"This 'as nothin' to do with Char'ie."

"Sure."

"It ain't!"

"Dean, you don't have to be a part 'a this. Sam and I can deal with it. The job should be done soon, anyway, if Gabriel owns up to what he sent."

"I CAN HANDLE IT!" Dean yelled, slamming a fist on the table.

Bobby looked as though he wanted to yell as well, but stayed quiet, just staring at Dean.

"I'm going to bed," the older man shook his head, leaving the library.

Dean swiped the paper he'd been looking at off the table, leaving it a crumpled mess of sheets on the floor. He headed for the bathroom, wanting to throw some cold water on his face and forget about the whole conversation. As he walked, he noticed the metal door that he knew to contain a prisoner inside--Castiel, probably asleep in the pitch-black room. Dean opened the little window in the door quietly, peeking through the small bars. A scattering of light from outside threw itself across the tiny cell. There he was--asleep on the floor, hands cuffed. 

Dean looked at the little window, noticing the hinges on the cover as weak and rusted. Eyes glazing over with anger, he yanked out the pins holding the hinges on and tossed them across the room, the cover with them. They clattered across the hard flooring. Dean looked through the window, now free of a cover and standing out on the solid door, the outside light still illuminating the room with an almost comfortable glow inside.

"Some people deserve a little light," Dean grumbled, and turned away, determined to not think of his past.

**Notes for the Chapter:**

> I'm gonna go eat a brownie and get a head start on the next chapter :P


	9. Chapter Eight

**Notes for the Chapter:**

> Hey, I'm so sorry for not being around for such a long time. I was distracted by life and NaNoWriMo!

_July 4th, 1926_

Sam Winchester strolled down a busy avenue. Children were running down the tree-lined pathway, holding sparklers and little Americana flags, which fluttered in the wind. A young teen boy bumped into and ten brushed past the younger Winchester, followed by a woman frantically going after him. Sam stumbled slightly.

"Jack!" The girl called out, reaching for him and managing to catch the back of his tan collared shirt. The boy, Jack, stumbled backwards.

"I'm sorry, Jessica," he said immediately, standing to face her.

"You should be apologizing to the man you just rammed into, silly." She shot an apologetic glance to Sam, who was standing near a brick building. Sam attempted to find words to say it was all fine--this girl, Jessica, was quite beautiful, and she looked around Sam's age; 16 or 17.

"I am very sorry," Jack told Sam solemnly, "I was only running from my sister as a game, and I did not mean to run into you."

"It's fine," Sam was finally able to say, tearing his eyes away from Jessica, "It was an accident. No harm done."

Jessica sighed in relief. "Well, I'm glad to hear it, Mr.--?"

"Sam. Sam Winchester." _Shit,_ why did he just give his full name? That was a severe violation of the gang. If Dean were there, he'd have either kidnapped Jessica and her brother and ripped Sam's head off, or have just ripped Sam's head off.

"Nice to meet you, Mr. Winchester. I'm Jessica Moore, and this is my brother Jack."

Sam could see little similarity in the two, save for the light-colored hair. He shrugged it off, deeming that unimportant. Jack stood modestly, somewhat behind Jessica.

"Nice to meet you, Mr. Winchester," he echoed Jessica.

"Well, it's nice to meet the both of you," Sam replied, trying to look easygoing.  He checked his wristwatch briefly: 2:04. _Ah..._ "I have to go, but maybe I'll see you on the streets?"

"Alright, that would be nice," Jessica smiled kindly, taking Jack by the elbow and turning to go across the street, where traffic had paused.

Sam stood there for a moment. _That happened_...he really hoped that he would see those siblings again.

Mainly, Jessica Moore.

~~~~

Dean yanked open Castiel's door. "Hey."

"Hello to you, too." The kidnap-ee still sounded stiff towards Dean when he spoke. Of course, he had all rights to be--being kind to the person who locked you up in a cell for no reason wasn't a common trait. It certainly wasn't a trait Castiel Novak had.

Dean grabbed Castiel's hand and yanked his arm forward abruptly. Castiel almost fell out of the chair.

"What are you doing?"

"What does it _look_ like I'm doin'?" Dean replied gruffly, taking out a key and inserting it into the locks of the handcuffs. "No ropes. No cuffs. Go wild."

Castiel merely sat there, giving Dean some sort of mixed face between confusion and relief.

"Am I...free?"

"Uh..." Dean felt awkward. Of _course_ he would ask that. It was natural. "Not exactly. The deal's still going through."

"I thought my brother contacted you?"

"Neither your father nor you brother have sent anythin' since."

"So...I'm stuck here." The Novak boy's shoulders slumped.

"No need to get so down. You know what? I'll be right back."

Dean went to the door, exiting and starting to close it. Castiel suddenly noticed something.

"Hey, Dean, the win--"

Dean looked over his shoulder, partially visible through the window, which was no longer barred nor covered.

"Never mind," Castiel shook his head. "It's nothing." _It's something. Something indeed._

~~

Dean sat across from Bobby in the library.

"Somethin' ya want, boy?" Bobby looked up from his research. It was all he seemed to be occupied with, lately. 

Dean just sat there, trying to remember how he was going to propose his idea.

"Well," The older man raised an eyebrow, "Spit it out."

"What if we...moved Cas--uh, Castiel?"

Bobby gave Dean a grim look. "Moved him...where?"

"Well, we have so many rooms, and from the looks of it, he'll be 'ere for a while, so--"

"Do you _remember_ what happened to the last person you got close to? You can't make friends with the people ya kidnap, Dean. It's common sense."

Dean grimaced, now. "I get it. I remember what happened, and damn well it was my fault, but--"

"But ya wanna make the same mistake _again_? You know that this'll get out, somehow. Going easy isn't what goes good for a gang. 'Specially not the Hunters! You got a girl _killed_ , Dean, and we were so close to finishing that deal. We had a ransom at our _fingertips_."

"I know that, Bobby, but this is different. Cas ain't gonna get himself killed!"

"Well, you can't very well predict if someone's gonna get stabbed in the stomach while they're off to the bathroom, Dean!"

"I get that!" Dean yelled, standing and grounding his hands firmly on the table. "I didn't try t' get Charlie killed! None of us did! But it happened, she's dead, and now I'm trying to help someone else! And maybe he'll die, too, but ya know what? At least I _tried_ to help him, like I _tried_ to help her!"

Silence prevailed for a few moments. Bobby sighed and leaned back. Dean stood up straight, glaring at Bobby.

"You happy? I said it. I got Charlie killed. I tried to help her. She died. All my fault--but you know what? I'm gonna try again. And again, and again, because what we're doing here--" Dean looked away. "Bobby, what we're doin' here ain't right." He turned and walked away.

~~

Sam entered Harvelle's, his hat tipped over his face slightly. He took it off, grateful for the protected feeling the speakeasy brought him. It was _mildly_ safe to talk freely here, especially at the time he was there--around midafternoon, when there were very few people around to bother him.

"Well, ain't this a rarity," Ellen quirked an eyebrow as she watched Sam walk quickly over to the counter and sit at a stool. "Can I get ya somethin', Sam?"

"Just a regular bottle." He sighed.

Ellen nodded and set down a cooled bottle in front of him. Sam seemed to contemplate the amber liquid within the clear glass, as though trying to drown his mind.

"Somethin' wrong, Sam?" Ellen gave him a concerned look.

"It's just...nothing, I'm just been thinking."

Ellen leaned over on the table. "'Just been thinking', yeah. That's the cue for a long conversation about your life-happenins'."

Sam gave her a look of slightly amused understanding. "Yeah. Well...do you ever question the...the moral value of what you're doing?"

"What, you mean runnin' an underground and illegal bar and holdin' my breath until the coppers catch me? All the time."

"Kind of like that. You know about..." He glanced around quickly, " _Castiel_ , right?"

"Of course I do. Your brother can't keep his mouth shut about 'im after the first five shots, and Bobby's been around a few times, too."

"Well, he's been causing some mayhem, I guess. Dean...I think he wants to pull another 'Charlie' with the whole incident."

Ellen grimaced. "That poor girl."

"Yeah..." Sam shook his head. "But now, Cas could be in danger. You know there are people who target our gang. Hell, they target our targets, just to get a good laugh and see our faces when they turn up dead. And Dean just wants to help, but...well, you know, I don't wanna leave people locked up, either."

"Have you submitted the ransom again?"

"No, not yet. That's not like us."

"Sometimes ya need to reinstate the request. Hell, Mr. Novak migtha forgotten about his kidnapped son. He's probably occupied with getting Gabriel to inherit the business."

Jo sauntered over with a laugh. "Yeah, 'cause you're all into the latest Novak family gossip, aren't ya?"

Ellen rolled her eyes. "It's worth keeping up with the city, for incidents like this when you gotta help someone."

Sam nodded. "Thanks, Ellen."

"Anytime, Sam."

~~

Dean opened Castiel's door again. "Follow me," He whisper-shouted.

Castiel looked up from where he was sitting on the floor. Shakily, he stood.

"Why should I trust you?" Castiel's eyes narrowed.

"You shouldn't," Dean shrugged, "But either you follow me, or you stay in here until we get your shit father to pay up."

Castiel grimaced and followed Dean. "Dean...thank you."

"Anytime."


	10. Chapter Nine

**Notes for the Chapter:**

> Sorry! Sorry. Late again. High school--High school is scary. Stay away from it.

 

_July 7th, 1926_

Sam, Dean had noticed, was very distracted.

The teenage Hunter had been wandering aimlessly, researching things they'd closed on _weeks_ ago, and even forgetting what he was going to get when he walked into a room. Sam. _Forgetting._

After another hour of watching his brother muttering to himself and not knowing what he was doing, Dean decided to be the better man and intervene.

"Hey, Sammy, you alright?"

Sam looked over at his older brother. "Oh, yeah, I'm fine. So get this, the Knights of--"

"Cram it, I don't care about the Knights of Hell right now, I'm worried about _you_."

"What about me? I'm just--" He held up another journal of the millions on the shelves, "Researching."

"Yeah, and checkin' in the section labeled _'Closed Cases'_. Last thing I remember, the Knights are still on our tails, unless ya ended them when I wasn't lookin'?"

Sam grimaced. "Ah. Right." He replaced the tattered journal on the shelf. "I'll just go look on the other side, then." He started to push past Dean, but the latter grabbed his arm and pulled him back.

"Not so fast, Sammy. Tell me what you're doin'."

"I told you, I'm--"

"What you're _really_ doin'. You've got this lost-puppy look; more than usual, I mean."

Sam gave him a 'no need to be rude' face and sighed. "Really. It's nothing." He pulled away from Dean and walked out of the library. 

~~~~

Castiel sat in the 'guest bedroom' of the Bunker, blankly staring at a wall. It's not like he had much else to do. For a fair while, he had enjoyed the comfort of laying on an actual bed, but that had passed after he thought of the fact that he was _still_ a prisoner here. That had dampened his happiness, as it always did.

Regardless of being the person who had kidnapped him on the street, Dean seemed alright. Well, okay, maybe 'alright' wasn't the definition of  gangster and kidnapper, but he was better than the others. When Dean was around, Castiel felt...human. Like he still existed, even if his father had seemingly forgotten about him. 

Over the past few days, Dean and Castiel had more chances to talk. Just...talk, about life, about whatever. Dean often asked the youngest Novak about life in the mansion and living under his brothers' shadows. Castiel was careful not to reveal too much information, as it could be (and probably _was_ ) a simple way to squeeze valuable information out of him. Maybe this was benefiting Dean just as much as it was benefiting Castiel.

Castiel mentally scolded his own thoughts. This wasn't beneficial at all, most certainly not to himself. He had been kidnapped! He should be kicking and screaming every time a Hunter was in sight! He shouldn't be feeling so relieved...so oddly _safe_...

But yet, he did. He felt more safe then he ever had at home, surrounded by superiors. Even his sisters, his _sisters_ ; they were better than him. Hell, Naomi was a better businessperson than anyone in the Novak household. His braindead father just had to look up once in a while and notice that. But no, he couldn't; everything was on Gabriel's shoulders. Gabriel was going to inherit the business, the mansion, and every single person working at the factories, as though those people were...as though they were just...

"Slaves," Castiel muttered to himself. "They're all treated like slaves."

"Who?"

Castiel hadn't even noticed the door open, but there it was, and Dean was standing in the opening. Another thing Castiel hadn't noticed was that he himself was pacing back and forth, and he could feel the conflicted expression etched across his own face.

"Nothing, Dean. I was just thinking of my father's business."

"Ahh," Dean said with understanding in his voice, "You mean his lil' slave workers, runnin' around and doing' his bidding in his grand factories because he promises them a peaceful life of well-paid work? That damned grifter..."

Castiel's soft eyes turned to stone. "My father isn't a 'grifter'. He is just...trying to do what is best for the family."

"Scratchin' cash off of other people, with no pay in return? Sounds like a great guy."

"He is a wonderful man," Castiel said through gritted teeth, "When he wants to be."

"Sure of it."

"Either change the subject or go away."

"Damn, and here I am thinkin' _you_ were the one being held hostage. Alright. Tell me about your siblings, again."

Castiel crossed the room again and sat at the edge of his bed. Dean pulled up a chair.

"We've already thoroughly discussed this."

"Well, maybe I just like hearin' you talk," Dean half-laughed.

Castiel didn't know why, but he could feel the blood rushing to his cheeks. "I sincerely doubt that."

"Don't," Dean replied simply, shrugging and sitting back.

A voice was suddenly calling down the hall.

"Dean!" Bobby's gruff voice drifted in through the closed doorway, "We got mail!"

" _Useful_ mail?" Dean called back, grimacing slightly as he stood and went to the door. It opened, and closed, and Castiel was alone again. He stood and pressed against the closed door, listening for voices.

"Damn straight, it's useful! We got somethin' from Garth, about that one case a couple towns over..."

Ah. Just 'Hunter' stuff--no news about the Novaks. With a defeated sigh, Castiel went back to his bed and sprawled across it, then repositioned so his legs were crossed and his hands rested neatly on his stomach. His buttoned-up white shirt was starting to feel stuffy. It was a bit large. It didn't even belong to him--he'd found it in the closet while looking around his room. The change of clothes was nice. There were a couple sets of everyday wear, laid out in the dark, wooden box as though he was meant to find them.

Maybe he was. That was nice, too.

As he lay on his bed, the kidnapped Novak could hear the various, semi-usual sounds of the resident Hunters hustling and bustling about, getting ready to go somewhere or other. He heard something fall, and someone--probably Dean--swearing loudly. Then, several doors were opened and closed several times, and all was quiet again.

This left Castiel alone with his thoughts.


	11. Chapter Ten

_July 9th, 1926_

His thoughts, Castiel decided, were not very kind to him.

It was especially bad when he slept--little thoughts, little, devilish thoughts, creeping into his brain and overshadowing all of the decent thoughts he tried to hold onto, such as:

_It'll be lovely when you get back to your family._

As opposed to:

_Your family doesn't need you._

It was a constant back and forth argument, silently eating away at his sanity, which had already waned from the moment he had forcefully stepped foot into the Bunker.

_Your father misses you._

_Your father is too busy with work to remember you._

_Gabriel will be happy to get you back._

_You're not going back._

_At least he_ would _be._

_How do you know?_

_Naomi might be kind to you when you get home._

_She's not kind to anyone._

But there were more thoughts. Worse thoughts.

_Why don't you just end this now?  It would be a lot easier._

_That's not a way out. That's something you'd regret._

_There won't be time to regret a bullet in your head._

_God will punish me._

_God's abandoned you._

_..._

_God left you a long time ago, when he made your own father forget about you being locked up here._

_It's not that bad here, actually._

_You're right. It's not that bad here,_ 'Cas'.

Castiel's eyes snapped open, wide and all-seeing for a moment as panic filled him. _Cas. Cas. Cas._ He'd gotten that nickname before, but when he heard it in his sleep, talking to himself...it wasn't the voice of a sibling. He shook his head, sighing. This place was messing with him. 

_It's not that bad here, Cas._

He groaned and laid back down against his bed, pressing the heels of his palms against his eyes. A sharp tap sounded on the door, and before he could reply, it busted open. Typical. 

"Mornin'," Dean's gruff voice greeted him, and a small bowl of oatmeal was set on 'his' desk.

"Good morning," Castiel replied in careful words, sitting up and swinging his legs over the side of the bed.

"Can't talk this mornin'. Got a job to do."

"That's fine. I didn't think that most kidnappers and ransom-holders stuck around to talk with their victims, anyway."

"C'mon. We treat ya nice enough." Dean turned, leaning against the desk, now.

"Yes, nice for a gang member. Nice for a criminal."

"Aw, thanks." Dean smirked. He started towards the door, and gave Castiel a firm pat on the shoulder in passing, before saying, "See you later, Cas."

The door shut tightly.

_Cas._

\---

Dean rounded a corner, hand on his gun. The tension in the air was as tight as a violin string, and the faint sound of whimpers was present in his ears, getting louder as he grew nearer to the location of his daily 'meeting'. 

He peeked around the next corner, and saw just who he had been expecting.

"Crowley," He growled, "let her go."

"Oh, my," The accented man raised an eyebrow, "Whatever shall I do? Big, strong, thick-skulled Dean Winchester is here to beat me up again. Oh--sorry, if I recall, was it _me_ who beat _you_ up last time?"

"Shut your face and give me the girl!" Dean yelled, raised the gun and motioning towards the girl kneeling next to Crowley, bound tightly with ropes, crying softly. Her wavy hair was falling out of its braid, and she was wearing a rather short white nightgown. 

"Oh, I'm not just going to _hand her over_ ," Crowley laughed falsely, "Not after all the trouble I went through to get to her. Tried to just take her in her sleep, but _no_ , the little bitch couldn't comply that easily. Took three of my men to bind her."

"You're sick."

"Not as sick as the man currently holding the son of the most powerful man in New York _captive_."

"You're forcefully holding a _girl_ captive, and in terrible conditions."

"On what grounds can you complain of 'terrible conditions'? I've been in your resident jail cell before, when your shit of a father was running that place you call a 'gang'--not exactly top of the lot, Squirrel."

Dean rolled his eyes. He had been given that godforsaken nickname years ago, while going with his father to meet Crowley for the first time, when they were all trying to get along. Before they became archrivals. 

"Besides, this little lady doesn't have any complaints. Do you, missy?" He looked down at her. Fearfully, the girl shook her head, tears streaming down her face as she whimpered again, looking towards Dean desperately. "Exactly. Although, I guess I couldn't say the same for--what's his name?--Castiel."

Dean gritted his teeth. "Leave Cas out of this."

" _Oh-ho,_   you're on _nickname_ terms, now? Last time you held someone for ransom, you started calling her _Char_ , and she was dead the next week, wasn't she?"

"Crowley..."

"Yes...help me remember, did I slit her throat or shoot her?"

Dean tried to contain his anger.

"No, didn't I do both? Yes, I can still remember her screams--"

"You sick son of a bitch!" Dean yelled, and launched himself at Crowley. Crowley stepped sideways quickly, and Dean landed hard on the ground. However, the Hunter used his position to his advantage, and he kicked at the other man's ankles. Crowley fell near him, and Dean pushed himself up with the wall, landing a foot on Crowley's chest and holding the gun  just above his head.

"Let's not be too hasty, Squirrel," Crowley chuckled, "You want to know why I'm not in Chicago, don't you?"

"Bobby said you had unfinished business." Dean thought about the conversation he had had with the older Hunter yesterday evening.

_\--_

_"Dean, come look at this."_

_Dean hurried over to Bobby, who was inspecting a note on the table._

_"It arrived this morning. Take a look."_

_Dean inspected the note, which had presumably been written with a typewriter._

_'Hunters--_

_They're here. Chicago's here. All three branches of Hell--Knights, Hounds, Demons._

_They've got unfinished business._

_\--K.T._ '

_"It's that kid again, the one who's been tipping us off._

_"K.T....any idea who that could be?"_

_"No idea, whatsoever. But what I do know is that if this is true--and everything_ he's _sent so far has been--we're in for some major trouble._ "

"Don't you think that's rather open-ended? Unfinished business. I could have forgotten my weekly groceries.

"Don't be smart with me, Crowley!"

"My business is my own. My own, and your dead father's. Now, come along, Dean--let's strike ourselves a deal, or your own precious Hunters could be on the line, not just this worthless girl."

Dean reluctantly released the leader--'King'--of the Gangs of Hell. "You just got 'er to lure me here, didn't ya?"

"A bit slow, aren't you? Yes, I did, and I'll continue to hold her until you get me what I want."

"Alright--what do you want?"

"Your father's journal."

Dean's blood froze cold. "You're insane. I ain't givin' you my father's _journal_."

"Then I'll just have to do to her what I did to Charlie, won't I?"

The girl started shrieking through her gag, sobbing and shaking, wrestling furiously with her bindings. Dean felt his stomach twist. He had to get that girl out of here--she couldn't be much older than Sammy; fifteen or sixteen at the oldest.

"Let me talk to her," Dean demanded.

"As you wish," Crowley smirked, and whipped off the gag with one fluid motion. 

The girl gasped for breath. "Please, please, let me go..."

"Oh, dearie, I thought we were past this point," Crowley muttered distastefully. Dean glared at him, motioning him to leave. Crowley shrugged and went around the corner, but Dean could feel him still watching.

Dean knelt in front of the shivering girl and lowered his voice. "Listen. What's your name?"

"J-Jessica. Please, get me out of here..."

"Alright, Jessica. Are you that hurt?"

"M-my wrists ache...my feet...please..."

"Okay. Nothing broken?"

"No...please, I have a brother. Jack...he...he won't be alright, not without me."

Dean let out a breath. She had a brother--he had to help her. But he couldn't give up his dad's journal...

"Please, help me out...give him what he wants, I'm begging you!"

"I'll get you out of here, Jessica," Dean nodded, rising to his feet. "I promise."

He went towards where he had seen Crowley go. Sure enough, he hadn't gone far.

The look on his face must have told the 'King' everything.

"I'm glad that we have a deal."

 

 

 


	12. Chapter Eleven

**Notes for the Chapter:**

> An OC is briefly mentioned in a flashback. They will not be an important character, and will only possibly occur in later chapters, also in flashback form. Sorry if anyone doesn't like this.  
> Also, I forgot to post a chapter a while back! It is now in the chapter list, noted as 'previously unpublished'. I'm so sorry that I missed that!

_July 12th, 1926_

Dean was in the library, ruffling through pages and pages of books, trying to find...well, something. Anything, really, that could _save that girl_. 

She was innocent. Perfectly innocent, and he hated that. And she had a _brother_. A younger brother. If Crowley had captured some ragamuffin thief, Dean would have easily been able to walk away, John Winchester's journal still safely and securely in his possession. 

Of course, though, Crowley had captured an innocent girl on purpose. He _wanted_ Dean to feel conflict. That's how Crowley worked. He had nearly broken Dean's own father before, physically _and_ mentally, after a slip-up while the Winchesters were trying to sneak out with a pricey artifact from the King's collection. That artifact could have bought them a fortune, and the gang could have thrived from it, but the Hounds were waiting for them at the doorway, their dark blue suits a mark of impending disaster...

Dean shook the memory from his head. It was bad enough to think about his dead father, but it was even worse to think about the _bad_ times. Not that there were many good times...

Back to the point. Dean _had_ to, just _had to_ find something else to trade with Crowley.

"Hey, Dean?"

Dean turned his head to find his younger brother just outside the library entrance.

"Yeah? What's up, Sammy?"

Sam took a beat, and then walked up next to Dean, leaning against the table where Dean had about fifty books laid out, open to various pages.

"Are you busy?"

"Uh," Dean looked around at his paper catastrophe, "Nah, does it look like it?" He replied, sarcasm quite evident.

Sam nodded, and stood up. "Sorry. It can wait."

"Wait, wait, wait!" Dean turned around as Sam started walking away, "I have time. Seriously."

Sam turned back and arched an eyebrow. "You sure?"

"Yeah! Yeah, I always got time for my little brother."

"You say that, and yet you constantly shoo me outta the room--"

"Past is past, Sammy. I ain't doin' that now. Stay." Dean sat down, and pointed towards the chair across from him.

Sam sighed and sat down opposite of him, silent.

"So?" Dean encouraged.

"Just--ah, it's stupid."

"Whatever it is, it ain't stupid."

Sam didn't speak for another moment, but then finally opened his mouth. "Are there any rules here about...I dunno, seeing a girl?"

Dean shrugged. "I mean, I see Lisa all the time--"

"Seeing a girl, but _not_ just to sleep around."

Dean laughed, now. "Yeah, you're right, this is stupid."

Sam's face fell.

"Never mind, I'm kiddin', I swear it!" Dean quickly backtracked, seeing how sad his younger brother now looked. "Look, Sammy, seein' someone--it's just not safe. I mean, it's different if it's someone who's sorta underground, or part of the gang, but...what are you thinkin'? You got someone in mind?"

Sam smiled softly. "Yeah."

"What's 'er name."

Sam's smile couldn't be contained. "Jessica."

Dean's heart stopped for a beat. He didn't say anything for a moment.

"Is something wrong, Dean?"

"No! No, I just...nothin', I just remembered somethin' Bobby wanted me to do. Not important. Uh...what's this Jessica girl like?"

"Oh, she's great. Around my age."

Dean held his breath.

"She has this curly hair--"

This was horrible.

"Oh, and a younger brother. Jack."

"Jack..."

"Yeah. Dean, really, is something wrong? You seem...disturbed. Wait." Sam's eyes widened. "Do you know her?"

"Sammy..."

"No. No, you gotta be joking--Dean, how? _How_ do you know her?"

"Sam, I'm sorry."

"No. What happened to her? Is she part of a gang?"

"No, she's--"

"Is she hurt? Is she alive? Dean, please tell me that she's alive!" Sam was yelling now, standing, his hands balled into fists.

"She's alive. For now."

"Where..."

"Crowley's in town--Bobby told ya. And he took Jessica as bait for us. This...this explains how."

"Dammit!" Sam yelled, slamming a fist on the table. "I met her once, Dean. _Once_. We promised to meet again, but...why does _everyone_ that I go near get hurt? Everyone! _Dammit_!"

"Hey, hey, what's goin' on?" Bobby's low voice sounded from the library entryway. "What's all the yellin' about?"

"That girl, Jessica," Dean explained quickly, "Sam knows her."

"Well, shit."

Sam, looking thoroughly angry and upset, stormed out of the room. Dean heard three doors slam down the hall.

"He met 'er once," Dean shook his head, standing, his arms crossed. "And he's convinced that he's in love with 'er."

"He's just sixteen," Bobby sighed. "He'll get over this. It's tough luck, bein' in a gang. Everyone you know..." He trailed off for a moment. "Anyone you love, they get hurt."

"Damn right."

\--

Castiel was sitting at the desk, doing nothing. Just another typical day--including the yelling he was hearing down the hall. He heard heavy, angry footsteps storming closer to his room, and for a moment, he felt a pang of fear--but the footsteps moved right past him. _Slam...slam...SLAM!_ Three doors were furiously closed by the angry footsteps. 

Strangely, Castiel had been hoping that the footsteps were Dean, coming to talk to him again.

At that thought, Castiel's mind unwillingly floated to his childhood.

_"Cassie!"_

_Castiel turned to see a familiar face--a boy his age, the next-door neighbor. He was dressed sharply in a dark green suit, much alike all the other little boys in this rich, suburban neighborhood, but his messy, curly locks of gold set him apart from the crisply combed hair of every other child Castiel had ever met. His own black hair felt awkward and flat against his head whenever he looked at his friend._

_"I'm coming, Thomas." He hurried after the boy, who was a mere few feet ahead of him, but the short legs of an eight-year-old boy were not very efficient for running._

_"Hurry, Cassie, follow me--I want to show you something!"_

_Castiel followed Thomas around the next several winding corners. Soon, they were out in a small, open area, with a few trees sparsely sticking out. Wildflowers, though, seemed to thrive in this little patch of nature._

_"It's going to be a play-park," Thomas explained, sitting down in the grass, "But it's really pretty, now. Come sit, Cassie, before all the workers come tomorrow and wreck everything."_

_Castiel warmly smiled at Thomas and sat in the grass right near him._

_"The sky is so blue today, Cassie! Look! I think that's a bird, up there..." He pointed to a bird in a tree. "It's a bluebird."_

_"A bluebird?" Castiel's eyes widened, and he grinned. "I've never seen a bluebird!"_

_"Listen, it's singing--"  
The boys sat in silence for a moment, and sure enough, little twitters were sounding from the innocent bluebird. _

_"It's so pretty out today."_

_Castiel nodded in agreement._

_"It wouldn't be nearly as pretty without you, Cassie."_

Castiel's heart panged at the memory, as he thought about what had happened next.

_"Th-thank you, Thomas..." Castiel couldn't help the blush that hit him._

_"No, really, Cassie. Everything is blue today. The sky, the bird, and your eyes. Did you steal the sky and lock it in your eyes, Cassie?"_

_Castiel didn't know what to say to that. The eight-year-old shrugged shyly, and the other, his exact age, now looked embarrassed, as well._

_"I'm sorry. I just have a lot of things to say today, is all--"_

_"Don't be sorry!" Castiel quickly interrupted. "Maybe I did steal the sky. Can we play a game like that, stealing the sky? Like tag?"_

_Thomas smiled. "Okay. Let's play!"_

That wasn't the end. He wanted to stop thinking about it, but he couldn't. A few hours after their game of tag, everything changed. They had been sitting on the front step of the Novak mansion.

_"Cassie, do you like me?" Thomas inquired._

_Castiel blinked. "Yes, you're my best friend."_

_"That's good, because you're my best friend, too."_

_Castiel suddenly thought of something. "You know, my daddy said that mama was his best friend. He said that best friends like that should stay together forever."_

_"How do you stay together forever?"_

_Castiel and Thomas were both stumped at that. They sat for a few moments, thinking._

_"Oh! They got married."_

_"Oh, right. That makes sense. But can't only a boy and a girl get married?"_

_"Do you think it matters? I haven't met a lot of married people."_

_"Me neither. I guess we could get married, then."_

_"How should we get married?"_

_"I don't know. They make this big speech at weddings. I went to one once. The people are holding hands, and they say stuff to each other, and then they kiss."_

_"We could do that."_

_"Alright--you go first."_

_"Okay!" Castiel thought for a moment about what to say. "Thomas, you are my bestest friend, and I would like to marry you."_

_"Ca--Cast-ee--" Thomas gave up. "Cassie, same."_

_"Then it's settled."_

_They both leaned in to kiss each other--_

_"Castiel!"_

_The door had slammed open. Castiel scooted away from Thomas. Naomi stood there, hands on her hips._

Naomi's voice, however young, echoed in Castiel's head like a thorn bush beating against his skull.

_"That's so disgusting! Get inside. Father's going to be upset with you!"_

_Castiel cried softly as he was dragged inside by his older sister. Thomas waved at him, before running over to the fence where he often jumped over to get to and from his own house._

_That was the last time Castiel was allowed to see his best friend._

Castiel still hadn't seen Thomas since that day. It was a terrible memory. They were only children; how could they have known what marriage was? He only wanted to stay with his friend.

Still, he couldn't shake the fact that he hadn't felt like that around any girl. He never wanted to kiss the pretty girl he met when he was fourteen, or the young lady who had chatted him up at a business dinner last year. Maybe it was all coincidence. He also couldn't deny that he had felt more than awkward around the handsome boy who used to come over to clean with his mother; that boy who was just around his age. 

He thought about the Bible that his father had given him that fateful day with Thomas, and how he had quoted many passages. Rules from Leviticus, the story of Sodom and Gomorrah...Castiel had felt like a sin embodied. 

 _Forget that._ Castiel shook his head to rid himself of all these burdens weighing on his mind. _It's pointless._ There was no reason for this memory to surface now; it was only because he had been locked up in the Bunker for so long.

The door opened. 

"Hey," Dean half-sighed his greeting, closing the door behind him."

Castiel couldn't help the small, sad smile that appeared on his face. "Hello, Dean."

 

 

 

_  
_


	13. Chapter Twelve

**Notes for the Chapter:**

> Wow, the kudos and hits have really gone up! I'm so thankful for everyone that reads this.

_July 15th, 1926_

"We're goin' out."

Dean glanced at the gun that had just been thrown on the kitchen table in front of him, and then up at Bobby. "What? Where to?"

"T' get that girl, dimwit. C'mon."

"Are you sure about that? We still gotta find a way to get Crowley to let 'er go--"

"Look, it's either we go _now_ and get 'er, safe and sound, or we wait until the coppers find her, get her shot by a Hound, and get Sam even more upset than he already is. You say she got a brother, right? Don't ya think he's worried about 'er?"

Dean sighed. "Yeah, yeah. You're right." He picked up the gun and tucked it into his belt, and grabbed his hat from the stand in the corner. "Let's go. Sam comin'?"

"You think that'd be smart? He might get irrational."

"This is Crowley we're dealin' with. I'd rather have three against Hell than two."

"Yeah, you're right...I'll go get 'im."

Moments later, all three were heading down the street. 

"Wait!" Dean suddenly exclaimed. All three halted in their spots.

"What? You forget your gun?" Sam asked.

"No, it's just...we just left Cas alone in the Bunker.

"Yeah, like _he's_ gonna break out," Bobby chuckled. "That kid ain't got an ounce of strength in 'im."

"I'm more concerned about someone...I dunno, breakin' in."

"His family don't know where he is. That it?"

"Nah, I'm just thinkin' about...you know, Crowley, when I met 'im a few days ago, he mentioned Charlie, and--"

"Dean," Sam stepped in, placing a hand on his brother's shoulder, "He's just messing with you. Nothing will happen to Castiel. Charlie...that was a one-time mistake."

"How do you _know_?"

"You seem awful concerned about some guy we're keepin' for ransom," Bobby pointed out, huffing. "I understood Charlie, but this guy? All 'e does when I'm around is glare an' grumble. I wouldn't be too concerned if he disappeared."

Dean suddenly wanted to change the topic. "Never mind. Let's get goin'. We got a Jessica to get home."

Sam nodded in sturdy agreement, and the trio continued on their way to the King's lair.

\--

"Dean, MOVE!"

Dean rolled out of the as another gunshot blasted through the air. The abandoned alley that Crowley so loved to lurk in had few places for hiding, and the Hunter took refuge behind a metal trash bin. He looked over at Sam.

His brother was really tearing Crowley's defense up, shooting down his Hounds with the help of Bobby, Jessica standing right behind Sam with a look of horror and awe on her dirt- and tear-streaked face. 

Dean ducked out of cover to help his friends. The only ones left were Crowley and his 'best' Hound, a middle-aged woman that Dean knew he had met before. She went by the name of Juliet, and her dark blue suit made her short, blond hair stand out, like sunlight at nighttime. 

"Come and get 'im, _Hunters_ ," Juliet spat.

"Now, Juliet," Crowley _tsk_ ed, "Stand down. I think these boys only want to talk about our current _circumstances_."

"All we want is for you to hand over the girl without a fight," Dean snarled.

"I think we both know how that can be accomplished, Squirrel," Crowley raised an eyebrow. "Give me John Winchester's journal."

"The hell does a stupid journal matter to you, anyway?"

"Oh, I think you know."

Dean did know. The journal contained all the secrets of the Hunters--their locations, their members, and even details about the biggest cases they'd ever pulled off. More importantly to Crowley, though, the book also contained notes on the top gangs in America, including the Knights, Hounds, and Demons of Hell. 

"Hand it over, and I won't kill the girl," Crowley shrugged. "Simple."

Sam moved his arm behind his back and grabbed Jessica's hand, as if to make sure she was still there. "You can't have her."

"And you can't have the journal," Bobby added. "John didn't put it together to be used by the scum of the street like you."

 "So you let us go, and we won't kill _you_ ," Dean smirked. "Simple."

Crowley studied the trio for a moment. Next, chaos broke loose.

Juliet lunged for Sam. Bobby grabbed Jessica and pulled her out of the way of the Hound's wrath, and Dean shot at Juliet's hand-- _yes_. She screamed and dropped the knife that she had perched above Sam's head. It nicked his forehead, and the younger Hunter hissed in a breath, but he stood quickly, retrieving his gun from the ground. 

Juliet, done with cowering in a corner, leapt at Jessica, knife in hand. Thankfully, Sam had already anticipated this, and a resounding gunshot echoed through the alley and street as Juliet fell to the ground, bleeding from her abdomen. She coughed twice, blood sputtering up from her throat, before her head lolled back.

"You," Crowley blinked in annoyance, "You just killed my best Hound."

"Yeah, an' how about we shed some light through _you_ , next?" Dean glared. 

"Boys, boys, boys," Crowley shook his head. "When will you learn?" 

Three tall men in dark green suits suddenly appeared, seemingly from out of nowhere, but Dean quickly spotted the previously camouflaged door on the alley wall to the King's right. 

"Knights," Bobby muttered, "Damn it."

Sam reloaded his gun and started shooting again. Bobby shot twice, but let out a yell as a bullet hit his shoulder.

"Bobby!" Dean exclaimed, positioning his own gun again and making his way towards Jessica, who was being cornered by another Knight.

"I'm fine, get the girl an' get outta here!"

Dean ran up and slammed his elbow into the Knight's face, and the attacker stumbled back, bringing a hand to his bloody nose and already bruising cheek. 

"C'mon!" Dean shouted at Jessica over the yells and gunshots. He pulled her by the hand around the corner of the alley, trying to get ahead of any possible followers. Whenever he looked back, Jessica stared at him with wide eyes, looking dazed and terrified.

He kept running. He had to get her to safety.

They reached a more main street. They probably looked odd, a dirty, horrified girl running with a bloodstained man in a black suit. He stopped in a clear alley, and Jessica leaned up against him. He squeezed her arm in a comforting fashion.

"You're alright, now."

\--

"Thank you... _so_ much," Jessica said for the thousandth time, pressed up against Sam like a moth to a flame.

"It's just what I do."

"' _It's just what I do',_ " Dean mocked Sam quietly, "' _I'm just a cocky little sixteen-year-old who's taking all the credit._ '" 

Bobby snorted. "Ah, let 'im have the girl for once, Dean."

"Yeah, yeah," Dean laughed, leaning back against the wall of the Harvelle speakeasy.

Upon regrouping, the gang (and Jessica) had gone to Harvelle's to clean up and let Jessica know what was going on. Surprisingly, she took the gang situation rather well. 

"My mother used to know a guy--actually, well," She shrugged, still talking to Sam, "He was the guy who got her Jack, my brother. They were sixteen or so..." She shook her head. "It was a big affair. He was from some fancy family. Anyway, he was apparently into some deep, underground drug business. Never told her what, exactly."

"Huh," Sam had shrugged. "Wonder if my father knew him."

"You know, rumor has it...at least within my family, you know...that he was _Lucifer Novak._ "

Dean blinked and tuned in, leaning towards the table the two were sitting at. Jessica rearranged the brown skirt of the dress Jo had given her, having insisted that she was going to wear pants from that moment on and would no longer need 'nonsensical, cumbersome lengths of cloth'.

"That so?" Sam leaned closer to her across the table.

"Yeah--they had a swell time for a couple months, but as soon as my mother found out she was pregnant, he up and left. And he left the Novak fortune last year, you know, so she's always hoping he'll turn up again, even though she's got _my_ father, now."

"That's...terrible."

"Yes, and Jack feels awful, even though it was no fault of his."

"He shouldn't feel awful. Lucifer was exposed as a terrible person."

"Yes, but...you know, that was just the press. They exaggerate everything." Jessica sighed, leaning on her elbows. "Who knows what the real Lucifer Novak is really like?"

Dean had heard enough. "Jessica, I think it's time to take you home. Can you find your house from here?"

Jessica nodded. "You'll be coming with me, won't you?" She glanced fearfully at Sam.

"Of course I will," Sam rushed, "I don't want you getting hurt."

" _We_ will come with you, yes," Dean nodded, arching an eyebrow at his younger brother, who was too encompassed in staring at Jessica to notice his quizzical look. "Oh, an' Ellen?" He looked over at the bartender, who was cleaning out a bottle.

"What, you gotta 'nother complaint about our liquor today, Dean?"

"Yeah. Stop tryin' to give me coffin varnish. I know what your good stuff is like."

"Got it. Jo, can you write that down and put it in the fire with all of his other complaints?"

"On it," Jo replied from across the room, winking jokingly at Dean.

Dean rolled his eyes. "As always, good to see you, Ellen."

"You too, Dean. Stay safe, boys--and Jessica."

All four nodded and gave their thanks for her and Jo's help, before heading to bring Jessica home.

\--

After bringing Jessica home--which resulted in a tearful reunion with Jack, who Dean could _not_ stop staring at with awe--the Hunters were back at the Bunker.

"I'll call up someone downtown to station themselves around that building," Bobby reassured Sam again, "An' she ain't gonna get caught again."

Sam nodded with relief. "Alright."

Dean, meanwhile, made his way to Cas' room. He had a few questions about one Lucifer Novak.

 


	14. Chapter Thirteen

**Notes for the Chapter:**

> I think that I'll actually be finishing this pretty soon.

_July 16th, 1926_

Dean glared at Castiel from across the room, where Castiel was seated on the edge of his bed.

"So, you're tellin' me that you had _no idea_ that your brother's in a gang?"

"I swear, Dean, I didn't know."

"He's your brother, for God's sake!"

"I haven't spoken to him since he left the family!" Castiel protested. "He's hardly even my brother, anymore!"

"If Lucifer's involved in a gang, and his son's sister was kidnapped by another gang, and that _same_ sister is seein' _my_ brother...Cas, you got any idea how much of a mess this could be? You could be used to lure Lucifer into something. It could endanger _you_!" Dean huffed and crossed his arms, looking the other way.

Castiel swallowed. "I don't think that Lucifer hardly remembers my name. And why would you care if this endangered me, Dean?"

"Because--" Dean shook his head. "I--because if you're shot dead, there ain't a soul who's gonna pay to get just your rottin' body back!"

The words stung Castiel like hornets. "Right. Yes, the ransom."

Dean glared at Cas for a moment. He started walking towards him. For a moment, Castiel backed up, thinking that he might get punched. But then, Dean simply turned and walked out the doorway.

\--

_July 17th, 1926_

"We got another box to send out today," Sam informed Dean, lifting a decently-sized wooden box into his arms. "I bring it to the corner alley, right?"

"Yeah, and Garth's gonna meet you there."

"Haven't seen him for a while..."

"Coppers nearly got 'im. He had to lie low for a bit. Hey, tell me how he's doin' when you get back, 'kay?" Dean was curious as to how his fellow Hunter had escaped going to jail, mostly.

"Sure." Sam waved, nearly dropped the box of liquor, and caught it with the other arm. "See you." The door opened, closed, and Sam was on his way.

Dean was shuffling through pages and pages of requests for drugs, alcohol, and some discreet plans to 'get rid of' some other peoples' enemies when Bobby sauntered in with the morning mail.

"We got another letter from that other Novak guy, Gabriel," Bobby reported, "You might wanna take a look at this."

"About time," Dean huffed, tearing open the thin envelope with an anticipating swipe of his thumb. He plucked out the letter, which was thankfully on a small scrap of paper this time, but a full sheet, crisply folded in half. Dean flattened it out on the table.

_Shitty guys who took my brother--_

_Greetings. My father found out what I was trying to do with my bank account, and has now replaced it in his name. Supposedly, he's gonna get you guys to lower the ransom. Not sure how, but wait for that demand._  
  
I got some money stored in the next town over, so I'm gonna count on my buddies down there to help me out. I'm not gonna try and negotiate a price with you. I just want my brother back.

_Keep Cassie safe, or Lord help me, I'll make all your nightmares come true. I'm not a father's son. I'm not here to lower the demand on my little brother's life._

_-Gabriel Novak_

"Damn," Bobby shook his head. "He's determined. Nice t' know that someone's gonna pay up eventually."

"Yeah," Dean nodded, "I'm just wonderin' when. I don't think we can go much longer with Novak's cronies hangin' around the cops, tryin' to pluck off gangs."

"We'll just have t' hold fort for a while longer."

"Yeah...hey, is Sam back yet? That job shouldn't take long."

"It's Garth; he probably just stuck around t' talk."

"You got a point."

About a second later, Sam shoved the door open, closing it with a soft click. He gave Dean a brief smile.

"So get this," Sam started, "Garth actually was _arrested_ , but he later escaped from jail by _convincing the guard to let him out_."

"Wait, seriously?" Dean raised an eyebrow.

"I'm callin' bullshit," Bobby snorted.

"No, seriously. Apparently, he recognized the guy from some big bust about a year back, around the time Dad--uh, around the time Dad died. The guard was some big cop guy back then, but he made some sort of slip-up later on, and now he just guards the big house. Garth had some dirt on him from the bust. Supposedly, he had some guy cornered, but he talked to him for a bit and let him go." Sam laughed for a beat. "Garth scared him with that. Said he could get him fired from guarding, even."

"So you're tellin' me," Dean crossed his arms as he leaned back in his chair, feet on the table, "that the Garth _we know_ crushed outta the big house by _blackmail_?"

"Gotta say, I underestimated him," Bobby shrugged.

"Oh, yeah--Sam, look at this."

Dean held out the letter from Gabriel to Sam, who scanned over it quickly and looked back at Dean with a look of surprise.

"So, is this deal gonna be final? Do we have a deadline?"

"Deadline?" Dean thought for a moment. "I dunno about that. I mean, he says he'll get it to us, so we'll just wait and see, y'know?"

"You sure?" Bobby asked gruffly. "Aren't you all about that time limit stuff? I mean, Charlie's friends only had three months--"

"Yeah, well, you saw how that turned out, didn't you?" Dean snapped, standing. "Just--whatever. You can plan a deadline if you wanna plan a deadline, but I ain't any part of it."

With that, Dean left the Bunker. He needed a drink.

\--

Moments later, he stepped into Harvelle's, letting the scent of sweat, stale liquor, and fairly decent food wash over him. Not the best smell to anyone new, but to him, it was comforting. It meant Ellen, Jo, and illegal beer.

"Hey, Jo," He called to the blond, who was sweeping up a mess of broken glass and rejected alcohol, "Where's your mom?"

"Out back," Jo pointed to the general direction of the partially concealed back exit. "I think she's talkin' to Lisa."

"Alright," Dean smirked, thinking of Lisa. "Thanks."

"Yeah," Jo nodded. She turned to give him a smile, but he was already turned away, opening the back door. She sighed and looked back down at the shards of glass, sweeping them up and into the trash.

Dean grinned at Lisa as he noticed the brunette talking to Ellen just outside the speakeasy. He noted Lisa's black dress, covered in fringe and falling just above her knees, and how low the top dipped when the woman turned to smile back at him.

"Good evening, Dean."

"And to you, as well," Dean replied with a smooth voice.

"Save the flirtin' for her show break," Ellen interrupted, rolling her eyes. "Speakin' of the show--Lisa, I think we're about to get the evenin' crowd in. Do ya mind gettin' ready?"

Lisa nodded and headed back in.

"Only you this evenin'?" Ellen asked Dean, leaning against the door and therefore blocking him from getting inside.

"Yeah," Dean nodded. "Yeah, y'know, Sam's just workin' with Bobby on--"

"Hey, don't try t' trick me with the smooth voice thing."

"What 'smooth voice thing'?"

Ellen raised an eyebrow. "That thing where you act like everything's alright, when it's clearly not."

Dean sighed. "Listen, Ellen, everythin' is fine. I'm just dealin' with some stuff in the gang right now."

Ellen shook her head. "Alright, if ya say some. Go on inside." She stepped aside from the door. "Ya look like you could use a drink, anyway."

Dean gratefully obliged and stepped back into the speakeasy. In moments, Ellen had a cold drink on the counter for him. She stepped away again, and Jo took over bartending as the evening crowd started wandering in, some already drunk, and others looking for a way to drown their worries, much like Dean.

"Jo," Dean started, "Do ya ever worry that...maybe you're thinkin' about someone in the wrong way?"

Jo shrugged. "I guess so, yeah. What do you mean?"

"I mean, there's someone that's been on my mind, but I feel like it ain't right, the way I think of hi--of 'em."

Jo smiled softly. "Y'know, I think I get what ya mean. I find myself thinkin' of someone all out of sorts. You care t' tell who it is?"

Dean took a deep breath. "Jo, you gotta swear you ain't gonna tell a soul."

"Swear it on the Lord, Dean. You're worryin' me." She leaned forward, expression unreadable.

"It's...Cas. Castiel. The guy we--the Hunters--are keepin' for ransom..."

"Go on, Dean."

"It's just..." He shook his head. "It's stupid! It's bad enough I'm thinkin' of another _man_ this way, but Castiel? It ain't right. Not in any way. Around him, I feel like--it's how I felt, no, _feel_ around Lisa, but...not quite the same. You know, I can't believe I'm tellin' ya this."

Jo crossed her arms, standing straight. "Dean Winchester, you can tell me anythin', and it ain't gonna bother me. This is a revolutionary decade, and you're allowed t' like who ya like, or even love 'em."

Dean shook his head again. "This is the most pathetic thing--"

"It ain't pathetic, and you better know it."

Dean stood up. "This was a mistake--"

"What's goin' on over here?" Ellen inquired, arriving just when Dean didn't want her to.

"Dean?" Jo looked at him. "You ain't leaving yet. I don't think you believe me."

"Because it ain't somethin' I should believe!" Dean replied in anger. "I don't think you understand how wrong this is, Jo! How unbelievably wrong!"

"Dean, what's wrong?" Ellen demanded, grabbing his arm as he tried to walk away.

"Bein' crazy for man, Ellen, that's what's wrong!"

Ellen and Jo looked at him in shock as he stormed out of the speakeasy. The whole bar was quiet for a moment.

"If any of you say _anything,_ anything at all..." Jo threatened.

Ellen looked equally cross at the bar patrons, who hadn't spoken a word. "If any of you got a bone t' pick with Dean Winchester, you bring it to me, and I'll slap you right upside the face and kick you right outta Harvelle's."

That seemed to sedate the uneasy tension of the bar, but Jo still heard the murmurs of Dean's name after the silence disappeared.

\--

Dean entered Castiel's room. It was rather late--he had been wandering around the city for a while, trying to clear his head. Castiel was half asleep.

"Cas," Dean shook the other man's shoulder, "Wake up."

Castiel groaned. "What is it, Dean?" For a moment, he thought that maybe his ransom had been paid, but the look of frustration on the Hunter's face told him otherwise. No, not frustration--sadness. Deep sadness.

"Come with me. I'm gettin' you outta here."

" _What_?" Castiel tried not to raise his voice. "Did someone pay--"

"No," Dean replied firmly, cutting him off. "I just--please. Just follow me."

Castiel didn't need much coaxing. He longed to see his family again. However, there was something holding him back.

"Dean, do the other Hunters know about this?"

Dean was silent for a moment. "No. Okay? I'm just lettin' you go. And it ain't a trick. Call it a change of mind, maybe. Call it whatever you want--I just want you outta here."

Castiel nodded carefully and stood. He followed the quick-moving Hunter. He lost him for a moment in the darkness, but Dean then grabbed his hand--sending a jolt of surprise up Castiel's arm--and guided him to the door. It opened. Castiel gasped quietly as the scent of fresh air (fresh as it gets in New York) greeted him tenderly, inviting him out into the open for the first time in weeks.

"I'm gonna take you to the third corner," Dean instructed, "And then ya _run_. Just make a break for it. Please, just...fast as you can."

Castiel accepted this instruction and followed Dean. Corner one...now two...his heart raced, thinking of the freedom of the warm July air that was now on his skin.

Third corner.

"Dean..." Castiel looked back at the Hunter, who he could swear was almost _crying_ , a drop of water dancing in the corner of one eye, reflected by a streetlight nearby.

"Just go," Dean shook his head.

"Thank you." Castiel turned back for a moment, touching Dean's arm, before turning away and taking off into the night.


	15. Chapter Fourteen

**Notes for the Chapter:**

> Okay, yeah, I'm just trying to write this as much as I can before I forget the plot I wanted to follow.

_July 18th, 1926_

"Damnit, Dean, Castiel is gone!" Bobby yelled at the younger Hunter, who was quietly reading a newspaper.

"I know," Dean replied curtly.

"And you ain't worried?!"

"I let him go."

" _WHAT?!"_

At that, Bobby launched into a furious rampage about betrayal, being untrustworthy, and not knowing what you were doing. Dean barely listened.

"I'm sorry, Bobby."

"That it? You're just _sorry_? You lost us ninety _thousand_ bucks, Dean! An' Novak's gonna think he scared us off by not payin'. Our reputation is ruined!"

"Look, I don't give a _damn_ about your reputation, okay?" Dean stood, throwing the newspaper to the ground.

"What's all the yelling about?" Sam asked, wandering into the kitchen.

"Your brother here thought it'd be a bright idea t' _let Castiel go_!"

"What?" Sam looked at Dean with a mixture of shock and pride.

"I had my reasons," Dean replied to Bobby with equal anger, "Reasons you can't understand."

"Dean, here's your problem. Ya get way too attached to anyone who steps within a ten foot radius of you, s'long as they ain't from Hell or some other rival gang! What was it this time? You fallin' in love with some stuck-up kid of a millionaire?" Bobby seethed.

"Maybe I was!" Dean roared. "Maybe I was fallin' in love with 'im, and I had t' stop from fallin' in love with 'im, before I went crazy for bein' so stupid!"

Bobby and Sam fell silent.

"An' maybe you gotta realize that...well, sometimes, some people ain't mean t' be locked up somewhere. Some people have a purpose.

"Dean--" Sam tried to speak.

"Shut up, both of ya. I don't need you t' tell me that what I'm thinkin' is wrong. I already got myself to do that." Dean turned away.

Bobby sighed and left the room, going to the library. Sam grimaced and went down the hall.

Dean was left to think.

\--

Castiel knocked soundly on the door the Novak mansion. He thought about his appearance. He definitely felt weaker. He was dirty, and in sore need of a bath. He--

He didn't have time to finish his thoughts, because the door opened, and someone shrieked loudly.

"CASTIEL!" Hester yelped.

"Castiel? What do you _mean_ , Casti--" Naomi gasped as she met Castiel's eyes. "Hester, go fetch Father from the parlor."

Hester nodded and disappeared around the corner. Naomi hurried over to Castiel and ushered him in. "What happened to you? How did you get here?"

"They...let me go," Castiel panted, exhausted from his long walk home, in which he had gotten lost in the darkness a fair few times.

"Why would they let you go? Something's messing with you, Castiel...hurry into the kitchen, now, the others will want to see you; we were just finishing breakfast..."

No matter how long he had been gone, Naomi felt just as cold as usual. The energy in the kitchen, though, was a high buzz--all Novak siblings sitting around the table, staring at Castiel with looks of shock and relief.

"Cassie," Gabriel was the first to stand, "It's good to have you home."

He crossed the kitchen, pushed Naomi aside, and hugged Castiel tightly. The others soon stood as well, surrounding the previously lost man, a few crying or even laughing.

Mr. Novak entered the room.

"Don't crowd him," he instructed, and the others immediately stepped away. "Someone get him something to eat, that despicable gang must have starved you...you can get cleaned up while Anna prepares something--"

Anna nodded and hurried to the oven.

"--And then we can discuss."

Castiel nodded and practically ran upstairs to the bathroom. It was shiny a spotless, just as usual, and he turned on the faucet to wash his face.

After a good twenty minutes, when Castiel finally felt clean and was wearing respectable clothing, he retreated back downstairs. Most everyone was in the parlor, except for Anna, who beckoned him to the kitchen and gave him two rolls drenched in butter, a plate of pork, and a cup of milk. He ate quickly, as if the food would disappear, given long enough. Anna was smiling at him the whole time.

"It's so remarkable," She kept saying as she followed him to the parlor after he had finished, "Truly...praise God."

Castiel sat across from his wide-eyed family. He tried to skim over the isolated days, and told them simply that he was fine, that he had not been hurt (very badly), and that a Hunter had actually let him go.

Most of his siblings praised that fact as a blessing of God--"The Lord has changed his heart," one said--but Naomi dismissed it.

"You've had many long days," She interrupted, "And it may have been part of a plot."

"It wasn't," Castiel ensured, "Really, sister. Dean was kind to me."

"And the Devil may seem kind to sinners!" She announced shrilly, and stood. "They were messing with your head, Castiel."

"Naomi," Mr. Novak tried to interrupt, "You aren't implying that your brother is a sinner?"

"Why else would the good Lord bring this upon him? It was a punishment for his actions."

"Naomi, surely you don't mean that."

"It's purely what you've taught us, Father."

Mr. Novak instructed everyone else to leave the room. He started talking to Castiel about how he had been mistreated, and how they had to go to the police and tell them about what had happened.

Castiel shook his head. "I won't tell them anything, Father. I'm sorry. Dean was kind to me. I know that."

Mr. Novak, seeing he was getting nowhere, simply sighed and dismissed Castiel to his bedroom.

\--

_July 19th, 1926_

Dean paced his room. The day was new, and so were his worries. Yesterday had passed slowly, with Dean mainly sitting on his bed, drinking away the gang's small supply of poorly made alcohol, not daring to go to Harvelle's for fear of being mocked, and not wanting to go to the kitchen or library, for fear of worsening his argument with his brother or Bobby.

"Dean," Sam's voice interrupted his self-attacking thoughts, "You can't just stay in your room. I'm coming in."

Of course, Dean thought, he had broken the lock on his door weeks ago after locking himself out, so Sam easily entered with no trouble.

"Look," Sam started, "I'm proud of you."

Dean laughed hollowly and took another swig of alcohol. Sam crossed the room and knocked the bottle out of his hand, and it shattered on the ground.

"What the hell was that for?!" Dean yelled.

"You need to listen," Sam insisted. "I'm proud that you let Castiel go. He didn't deserve to be locked up, you're right. It's things like that that are why I don't really approve of the gang."

"Hey, I ain't leavin' the whole _gang_ \--"

"And furthermore, I think that you can fall in love with whoever you want. Everyone's being more free about things in this decade. It's revolutionary."

"You been talkin' to Jo? She said the same thing. All you kids like that, thinkin' everything's okay because it's some 'revolutionary decade'?"

Sam ignored the 'kid' comment. "I'm just saying, I think--did you ever...tell Castiel?"

"Ha! No. He would'a told the coppers and gotten me locked up, Sammy. You _do_ realize that--that homosexuality's illegal, right?"

"Dean, your line of _work_ is illegal. This, though...liking men isn't hurting anyone. I don't even know _why_ it's illegal."

"Because some stuffy law guy said so," Dean deadpanned. "Like all other laws." He tried to reach for another bottle on his table, but Sam blocked his hand.

"I think you should talk to Castiel."

"Not happenin', especially not now that he's back home. Besides, the guy hates me. I locked him up here for weeks, Sammy."

"Dean," Sam put a hand on his brother's shoulder, "I'm not kidding, every time that I mentioned you when I talked to Castiel, he smiled. _Every_. Time. If that's not some kind of love, I'm not human."

"Then I guess you ain't human."

"Just _go._ Find him. Talk to him."

"Alright, alright," Dean sighed, standing. "Hey, question--is Bobby mad?"

Sam's expression softened. "I think more so about you falling in love with a guy we were holding, than you falling in love with a man."

"Drop it with the falling in love stuff, Sammy, and wish me luck." Dean swung on his coat, placed his hat on his head, and left the Bunker.


	16. Chapter Fifteen

_July 20th, 1926_

Dean had arrived at the Novak mansion, and was currently trying to quietly circle the building, in order to find Castiel. It couldn't be going smoother--he had almost been caught looking through the windows at least three times. He hadn't actually gone over the previous day, as he figured he would give Castiel a day of peace before possibly ruining the other man's life and his own. Also, he had panicked and ducked into Harvelle's, sitting in a corner and ignoring the jeers of some other patrons. He was only back here on account of Sam's pestering.

But by some insane amount of luck, though, Castiel was sitting alone in the back gardens.

Dean sucked in a breath to calm himself. There was no one else in sight. He was on the opposite side of the fence, but he looked up and tried to get Castiel's attention.

"Hey!" he whispered.

The younger man jumped. "Oh, my Lord--" He backed away.

"Hey, I ain't here to take you back, just come _here_."

Castiel had a clear look of unease, but he was also intrigued. He'd be lying to say that he hadn't been thinking about the Hunter since he'd left. How could a member of a gang be so insanely kind to someone (most of the time) like Castiel, the son of a big company manager that all gangs hated with a passion?

Castiel finally allowed himself to go over to Dean. "What do you want?" He maintained a steady and safe distance.

"There's something..." Dean sighed. "I need to tell you something." He glanced down at the white fence dividing them.

"Yes..." Castiel replied carefully, trying to keep his voice from wavering.

"Ever since--Cas, ever since I really talked to you, _really_ talked, I've just felt...messed up. And that messed up feelin' got worse, and soon I felt _crazy_ whenever I was around you, and the whole time, I was guilty for keepin' you somewhere you didn't belong, so I let you go."

"What are you trying to get at, Dean?"

Dean was silent for a moment. "Castiel, I'm feelin' things I ain't supposed to feel when I'm around you. And it ain't right by any means, but damn it, I'm in love with you."

Castiel caught his breath. "You..." He fidgeted with his trench coat, his beloved trench coat that he had been happy to put on to go outside, even though it was a rather warm July.

"I'm sorry."

"No," Castiel shook his head. "Don't be sorry. I can't have anyone else feeling sorry for anything to do with me. Dean..." He stepped forward, leaned over the fence, and kissed the Hunter, right and proper.

Dean was soaring with conflicting feelings. He didn't think it was possible to think this many things at once. After a brief moment, Castiel pulled back.

"But...I don't know how we can ever...be together." Castiel shook his head. "I'm sorry, Dean."

"Right," Dean nodded, looking at the ground for a second, "That's what I was thinkin', too. Sorry. Just...I'm glad I got to do that, before..."

"Before what?"

"Before nothin'."

Castiel opened the fence gate a few wooden panels over, and stepped out of the garden. He faced Dean and leaned in to kiss him again, wrapping his arms around him. Dean did the same, but this time, all he could feel was sadness.

"Hey, Cassie, are you-- _holy_ \--" Gabriel stumbled back.

Castiel looked over at his brother with a face of shock.

"Gabriel, what's wrong?" Naomi stepped out of the house. "Castiel, who is that? Sir, why are you trespassing on our property?"

"He isn't," Castiel insisted. "Sister...brother, please."

Both Novak siblings looked shocked, now. Naomi stepped closer.

"I've seen you in papers...you--Castiel, you step away from him, this man is--! Oh, good Lord!" She notice their intertwined hands. "Castiel, you come inside, _now_!"

Mr. Novak had darted out of the door. "What's all this about? Castiel, are you--Gabriel, call the police. Call the police, that man is Dean Winchester!"

"Yes, he is," Castiel snapped, "And he isn't who you think. He is a kind man, Father."

"A kind man who led you on a path to sin!" Naomi shrieked. "Father, this man has turned Castiel to sodomy and the Devil."

Dean glared. "There might be a hell of a lot of things wrong with me, _sister_ , but Cas ain't a sinner."

"The police are on their way," Naomi threatened. "And you'll be arrested for the demon you are. Castiel, come inside."

"No." Cas replied simply.

"Castiel, stop being ridiculous. That is a dangerous man."

"I think you're more dangerous than him, Naomi. He was nicer to me than you ever were."

"False kindness, Castiel, when will you look _past_ disguises?"

"You wanna talk about disguises?" Dean raised an eyebrow, glaring at Naomi still. 

"I think I've already looked past your own, Naomi," Castiel said. "And I should have stopped believing your ways a long time ago."

"We can get you help, Castiel, and you can be saved! Step away from Dean Winchester."

"Don't talk to me about what God wants. If God is so kind, he will want me to be happy."

A loud, screaming siren was heard from outside the home.

"Dean," Castiel turned to the man he loved, "Run." He pressed a kiss to his cheek.

Dean nodded and took off, away from the mansion, away from police and misjudging sisters, and away from Castiel Novak.

\--

_We can't be together._

The words echoed in Dean's mind. Of course--they could never be together. He was in a gang. Castiel could be the respectable child of a millionaire. And besides, everything about it all was illegal. 

Dean laid back in his bed. Sam appeared in the doorway.

"It didn't go well," he stated simply, noting Dean's expression.

"Oh, it was fine for the first ten minutes," Dean sighed. "Then Gabriel Novak appeared, and everythin' went to hell. 

"What, did he call the police?"

"Nah, he just managed to draw out Naomi Novak, who started preachin' about how messed up I was, and then _Mr. Novak_ , of all people, walks out and has Gabriel call the police."

Sam was quiet for a moment. "I'm so sorry."

"It couldn't have worked, anyway. We were at least able to discuss that before I almost got arrested."

"Cops didn't follow you?"

"Nah, I got away." Dean sighed and sat up. "This whole thing's just...it's somethin' I wanna forget."

"I get that."

"But I don't think I can."

"I get that, too."

"Who am I kiddin'--Castiel's gonna haunt me for the rest of my life." As long as I let my life continue, Dean thought darkly. "You know what, change 'a subject. How's Jess?"

"She's great," Sam smiled. "She's safe, too."

"Two best things you want in a girl," Dean joked.

"Yeah."

_And in a guy._


	17. Chapter Sixteen

_August 4th, 1926_

Dean was wandering the streets of New York, going both nowhere and everywhere. He looked down at the list in his hand.

 _Crowley_  
Ellen and Jo  
Bobby  
Sam  
Castiel

A newspaper was tacked to a wall near him.

_CASTIEL NOVAK RETURNED HOME; CAPTORS STILL AT LARGE_

"Here we are," he sighed, looking at the beat-up sign that read 'The Devil's Workshop--Flamin' Deals-Sinners Welcome'. It was faded and barely lit by an overhead light. He knocked five times, in a familiar pattern, and the obscure door on the other side of the sign was opened.

"Winchester," A gruff voice greeted him, "What business do you have? You got that journal you owe the King?'

"Well, I think I'd like t' his _Majesty_ 'imself," Dean said mockingly. "Bring 'im out here."

The blue-suited man regarded him for a moment, and disappeared inside for another. Crowley suddenly appeared at the door.

"Come out here," Dean demanded, "Alone."

"Oh, how exciting," Crowley replied in a monotone voice. "Alright." He closed the door behind him and entered the dark alleyway. "What do you want, Squirrel?"

"I want you t' swear that you ain't ever gonna touch the Novaks, Jessica, her brother, or anyone related to her, ever again."

"Well, that was rather blunt." The King crossed his arms, looking at him as if he had just demanded Crowley hand over all his money--which was honestly about the equivalent. "I think you forgot to say 'please', even."

"I ain't lookin' for polite. I'm lookin' for a deal."

"Oh, a deal, really?" Crowley looked more intrigued.

"If you agree to never involve the Novaks _or_ Jessica's family in anything, ever again, I'll...I'll give you the journal."

"Is this that moment where I agree and then you back out? I don't think so, Squirrel. I never break my deals, so it's a bit tricky when you break yours."

"I have the journal, right here," Dean stated, opening his jacket to reveal the journal tucked in a pocket inside. "Now, swear it."

"Are the Novaks your little private property? Only you can kidnap them and tie them up for a ransom that never gets paid?"

"How did you--"

"Word gets around, Dean. Letting Castiel go? Not very smart."

"Don't you even _think_ about--"

"Oh, please. They're _such_ old news. Besides, Mr. Novak invests too much into stocks and businesses. I'd say that, in a few years, that whole empire will crash." Crowley shrugged. "I'll agree to your deal. Journal first."

"Write down your agreement, and I give you the journal."

"I need a surface to write on, Winchester, and that journal will do just fine."

Grimacing, Dean took out the journal and handed it to Crowley. Crowley took out a slip of paper and a pen, and wrote out the agreement, before handing the slip back to Dean.

"Don't lose that, or the deal is void," Crowley raised an eyebrow.

"Believe me, this deal ain't ever gonna go void. Not on the Hunters' watch."

\--

Dean let himself into Harvelle's. It was dark, so there was a fair handful of people in there. The Hunter went over to the bar and patted the table a couple times. Ellen appeared from around the corner.

"You doin' alright?" She asked, handing him a beer. 

"Yeah, I'm fine." He slid a few coins across the table.

Ellen wrinkled her brow. "Hey, you never pay me."

"Felt like it."

"Well, I ain't takin' your money."

"I ain't gonna need it."

That caught Ellen off guard. "Dean, you're really worryin' me. Take your money back."

Dean sat down and popped open his drink. "Thanks for beer."

Ellen sighed, leaving the money on the counter as she wiped off some stains from the wood.

Jo came over. "Hey, Dean," She greeted.

"Hey," Dean nodded in reply. He noted her baggy pants and top, and was quietly proud of her for starting her own little movement to go against society's incessant need for conformity. She hadn't worn dresses in a while.

"Dean, I'm going with some friends to that big restaurant downtown tomorrow afternoon" Jo suddenly said, "You wanna join? Jess is comin', and she invited Sam."

"You know, I don't think I can come," Dean shrugged, trying for a smile. He took out a paper and pen, and started writing.

Jo sighed. "Alright. Come if you can, tomorrow, then." She started needlessly reorganizing the bottles on the shelves. "What're you writing?"

"Nothin', just for business." For the next several minutes, he wrote, scratched things out, and wrote again.

Dean finished up his beer and tucked the folded paper back in his pocket. "See ya," he nodded to both women. "Thanks."

They said their goodbyes, and Dean turned to leave.

Ellen picked something up off the counter. "Hey, Dean, you forgot your pen..." He didn't reply. "Ah well, he can come get it tomorrow." She looked at the small, gold engraving on the surface of the black pen.

_Bobby Singer_

"Ain't even his," She chuckled to herself. She smiled fondly at the engraving for a moment, before tucking it into her pocket.

\--

Dean stepped into his room for a moment. It was a nice room, he thought, full of memories. When he was younger, he would wait up anxiously for his father to get home from whatever job he had. Sam would wander in sometimes, and Dean would walk him back to his room, or to the kitchen, where they'd have a snack. Sometimes, though, on bad nights when John Winchester got a bit too drunk, Sam would stay in Dean's room, where Dean would quietly tell him stories of better times.

"Hey, where were ya?"

Dean jumped slightly as he turned to face Bobby. "Oh, just out wanderin'."

"Dean, I just wanted t' say...I ain't too mad about you lettin' Castiel go. I think...in the end, that was the right thing to do."

Dean only nodded. "Yeah."

"And you know I ain't mad about you--I dunno, fallin' in love with 'im, or whatever. Right?"

Dean nodded again. "Thanks."

"Good." Bobby looked awkward. "You seem off, kid."

"I'm alright. I'll be alright, anyway. Hey, why don't ya go down to Harvelle's tomorrow? See Ellen? You haven't talked to her in a while."

Bobby shrugged. "Got busy."

"Well, she ain't too busy to see you. Mentions you sometimes."

"Really?"

"Yeah." Dean smiled a bit. "Really."

\--

Dean wandered past Sam's room, and quietly as he could, opened the door. Sam was asleep. Dean crossed the room to him, and noticed a note on his desk.

- _Pick me up at 12 and meet at Harvelle's with Jo_

_Love,  
Jess_

Dean imagined how his brother had gotten that note. Maybe Jessica was worried he'd forget, and wrote it out and gave it to him earlier that day. Maybe she kissed him. He thought of his little brother awkwardly turning away, and Jessica tapping his shoulder to tease him and say, 'Cash or check?' like Lisa sometimes did to Dean when he didn't kiss her before leaving. Before Dean met Cas.

Dean hoped that Sam would be happy with Jess. He opened his little brother's drawer and took out some paper that he knew Sam always kept under his now-favorite book, _The Great Gatsby_.

_Sammy--_

_Thanks for sticking with me. I can be a real piece of work sometimes.  
Keep Jessica around._

_\--Dean_

\--

Dean went to the kitchen, where he knew that his letter would be seen. He couldn't deliver it to Cas by hand--that was too dangerous. The house was under a constant watch by the cops. He folded the letter again, stuck it in an envelope, and wrote ' _CASTIEL_ ' on it in large letters.

"See ya, Cas," He smiled softly.

\--

He sat at the desk that Castiel had sat at. The room he had stayed in felt strange without his presence. He faced the wall, fiddling with the object on the desk. The object now in his right hand. The gun he was raising to his head.

The life he was about to leave, all because of one beautiful, strange man.

\--

_Cas--_

_Time is like money._

_You can invest in it, try to get more. You can save it up by working towards something, or waste it with careless things, like drowning in a bottle of bad alcohol. You can try to deal with it. You need time for everything._

_Like money, I never had enough._

_I didn't spend enough of it telling you how I felt._

_And now, well, I'm all out._

_I love you, Castiel Novak._

_\--Dean Winchester_

 

 

 


End file.
